Shelter Island Hotel – Luxurious Amenities Await

Looking for a wonderful Shelter Island hotel? We’ve got you covered. From the guest rooms to water views, we’re rounding up exclusive offerings at Seven On Shelter Island. 

When you think about what you want out of a Shelter Island hotel, various visions spring to mind. You might appreciate nearby beach access. Or you’d like a lovely swimming pool. Maybe you’re jonesing for a beautiful view from every guest room, or a short jaunt to nearby Sag Harbor. We get it. Fortunately, we’ve done the work for you. We’re outlining all of the wonderful amenities, specifically at Seven on Shelter Island, that you’ll find at hotels on Shelter Island. While you’ll have your choice between larger resorts and smaller bed and breakfasts, Seven on Shelter Island has the trappings of a charming inn with the luxe offerings of a five-star hotel. 

Read on as we outline everything you need to know about Seven on Shelter Island – the best Shelter Island hotel you’ll find in this charming seaside enclave. Whether you’re seeking proximity to the ocean, or just a good book and some peace and quiet, you’ll have an unforgettable time on Shelter Island.

A beautiful view of Seven, a the best luxury hotel on the island.

Why Shelter Island?

If you love the beach and a charming, slow-paced way of life, Shelter Island is for you. It’s got all the beauty of the nearby Hamptons, but it’s lowkey, easy, and filled with good vibes and good people. It’s got the best beaches on the East Coast, without the traffic or attitude. If you’re looking for an easy commute from New York or nearby cities, you should definitely visit a Shelter Island hotel. The island also has some of the best restaurants on Long Island, and there’s plenty to do both on and off the beach. The shopping is great and there are plenty of wineries nearby.

Where Does Shelter Island Get Its Name?

According to the Shelter Island Historical Society, the Manhanset Indians were the first to live on the island known as Manhansack Aha Quash A Womak, which translates to “Island Sheltered by Islands.” In 1620, King James I of England granted a large territory of land in North America, including Long Island and Shelter Island, to the Plymouth colonists. After the island changed hands, later to Stephen Goodyear of New Haven, it was sold as part of the Triangle Trade. Four sugar merchants purchased the island with 1,600 pounds of sugar. One of the merchants, Nathaniel Sylvester, married Grissel Brinley, and built their home on the Island. He settled here to run a farm that provided supplies for the sugar cane industry in the Caribbean. From this time on, the Island became known as “Shelter Island.”

Why Seven is the Best Hotel on the Island – The Amenities

Stylish & Luxurious Decor

The most stylish yet relaxed Shelter Island hotel is Seven on Shelter Island. Just steps from popular Crescent Beach, it’s got a charming “bed and breakfast” vibe with modern, upscale amenities you’d expect at a resort. The whitewashed farmhouse dates back to 1902 and was recently renovated by David Griffin, the celebrated interior designer, architect and Hamptons historian. Seven on Shelter Island owner Beth Swanström partnered with Griffin in evolving the space. Indeed, it has gone from a quiet, refined beachside inn to a luxury destination with art and design infused in every detail.

Inside, guests will be greeted by a stunning curation of art by Swanström, a former SoHo gallerist whose knack for contemporary art is on display throughout the hotel. The space features a series of works by Berlin artist: Sabine Dehnel, Marc Leavitt of Maine, Anne Lilly’s kinetic steel sculptures, and pieces by contemporary artist Billi Kidd.

Recreation & Relaxation

All you have to do is walk onto Seven’s hotel grounds to understand why it’s a great Shelter Island hotel. Outside, you’ll find a new, heated gunite pool flanked by a luxury cabana and custom outdoor pieces from Marcel Wanders’ Reverie collection in the form of black lattice lounge furniture with red accents. This collection is the first of its kind seen on the island. Just off the pool is an open air workout shed, with a cobalt blue enamel floor, free weights, a Peloton, MOMA water wheel rowing machines, Sonos Sound Bar, and large scale television for streaming workouts. Guests can work out freely or book private sessions with a licensed instructor who will join them at Seven.

Wellness & Meditation

The workout shed is also home to Seven on Shelter Island’s wellness offerings. There, guests can enjoy yoga classes – in both group and private sessions. There’s also meditation and breathwork, complete with tasteful moments at every turn. Guests can opt for sound healing baths with beautiful Tibetan bowls by Michelle Berlin, also known as Yogi Shelly, or enjoy a massage in the shed or out by the pool. The hotel also offers yoga and wellness retreats with Celine Antoine Yoga and many others throughout the fall and spring.

Luxury Accommodations

As far as the accommodations, both King and Queen rooms at Seven on Shelter feature luxe cotton linens, contemporary art, and sustainable bath products. by The Cold Spring Apothecary and Prè de Provence. With minimalist en suite bathrooms, flat screen televisions, and in-room refrigerators. There’s no end to comforts offered at Seven on Shelter Island. 

Bed & Breakfast

At Seven on Shelter Island, they spare no expense in offering French-inspired breakfasts. They serve French yogurts, fresh fruit, and bake bread every morning at the nearby Marie Eiffel café and market. Additionally, they can arrange for a mimosa if that is what you desire.

What’s The Perfect Day Like On Shelter Island?

Wake up and enjoy a beautiful breakfast at Seven on Shelter Island – either in the house, outside near the pool, or on one of its many patios. From there, take out a bike and cruise into town to check out the local bookstore or flea market. Stop at Marie Eiffel in town and grab goodies for your beach picnic lunch. Park your bike back at Seven and walk down to nearby Crescent Beach. Enjoy the people-watching at Sunset Beach and take a dip in the sound as the yachts make their way in for sunset. From there, it’s back to Seven on Shelter Island for a late afternoon swim, a cocktail or game of backgammon. Then it’s off to one of the many restaurants for a great night out on Shelter Island. Looking for some recommendations? This Shelter Island hotel has you covered.


How do you get to Shelter Island?

Shelter Island is only accessible by car ferry. The North Ferry departs from Greenport, NY and the South Ferry from North Haven, NY. The ferries are operated by two separate companies, so be sure to check the schedules and ticket prices, as they are different. If taking the Long Island Railroad to Greenport, you can hop on the ferry from the train station.

Do you need a car on Shelter Island?

A car is beneficial for exploring the island, but  Shelter Island Taxi can also take you around the island.

Is Shelter Island dog friendly?

Extremely! We love our furry friends at Seven on Shelter Island, and a number of beaches, hiking trails and restaurants also cater to dogs. There’s also a veterinary clinic on the Island, and 24-emergency veterinary care is nearby.

What are some popular beaches on Shelter Island?

Shelter Island is flanked by gorgeous beaches with a gentle wave that’s perfect for families. We’re surrounded on all sides, so if you drive down any road, you’re likely to end up at a beach. Two public beaches, Wades Beach and Crescent Beach, have lifeguards (10 a.m. to 5 p.m. in season), designated swimming areas, picnic facilities and restrooms. Parking permits are required at these and most other beaches.

What if I’m in a medical emergency on Shelter Island?

To respond to medical emergencies, call 911 and provide your location to the operator. The Shelter Island EMS crew will dispatch immediately, and they will ready a ferry for transportation to an off-Island hospital, if needed. If necessary, the Suffolk County Police Department will provide medevac helicopter service to transport you to the region’s Level 1 Trauma Center at Stony Brook University.

Can I bring my bike to Shelter Island?

With its challenging hills, shady lanes and sprawling roads that all seem to lead to water, Shelter Island is a great place to ride. Use common sense and follow the rules for sharing the road to avoid conflict.

The Best Shelter Island Hotel with Your Desired Amenities and Accommodations

However you plan your journey, Shelter Island is a beach and nature lover’s paradise with endless things to do. You’ll have your choice of where to stay once you arrive. But, for those seeking luxury amenities fused with an intimate sensibility of an inn, look no further than Seven on Shelter Island. The staff and team at Seven will ensure you’ll have the trip of your life. 

Shelter Island Bars and Restaurants – 9 Ideas for an Evening Out

Shelter Island bars and restaurants come in all types. Though the island is much more laidback and sleepy than the rest of the Hamptons, you can still find some lovely spots for a libation or two. Most of our bars are actually restaurants that offer delicious food, sophisticated ambience, and the chance to meet up with friends or a date. Stepping out is the perfect way to experience the island. Whatever you’re into, we’ve got the bar and restaurant for you.

If you’re seeking a lovely evening out, look no further than our Shelter Island bars and restaurants. You don’t need to head off the island to have a great time. On Shelter Island, we love to imbibe with locals and visitors alike. Whether you’re looking to sip some spirits in peace and quiet, or enjoy champagne and good vibes, we’ve got you covered. 

Read on as we break down the best bars and restaurants on Shelter Island and what you’ll find there. Whether you want to talk and dine, or just hang out, we’ve got it. Remember that we do not condone drinking and driving on the island. In fact, many of the following bars and restaurants are within walking or biking distance from Seven on Shelter Island. We are also happy to arrange a taxi service at your request. Or, if you decide to leave your car at a bar or restaurant, we will help you get it the next day.

1. Sunset Beach

35 Shore Rd, Shelter Island Heights, NY 11965

(631) 749-2001

Sunset Beach, one of the best Shelter Island Bars

This is one of the Shelter Island bars and restaurants that put Shelter Island on the map. It’s a scene-and-be-scene hot spot that starts with rosé at brunch. Stick around and you’re in for a treat. Come evening, the DJ starts spinning and it becomes a festive dance party. Like its name suggests, it’s the perfect sunset spot after a long day at Crescent Beach. You can catch the yachts pulling up for a glimpse, too. Luckily enough, Sunset Beach is just a five minute walk from Seven on Shelter Island, so you won’t need to drive there.

If you’re looking for food as well, order the steak or fish of the day and the oysters. For non-drinkers, the bar can make any of its drink specials without alcohol. Our preference? The Beach Melon with fresh watermelon juice. Make a reservation, otherwise be prepared to wait.

2. Shelter Island Craft Brewery

55 N Ferry Rd, Shelter Island, NY 11964

More a brewery than Shelter Island bar, this intimate spot specializes in small batch beer. Many flavors are made with local ingredients like beach plums and raspberries. It’s definitely worth a trip on a nice summer day. Order a fruity shandy and sit outside and play board games. Or, better yet, grab some local Mexican food at Maria’s Kitchen next door and bring it back. It’s the go-to spot on Shelter Island to try a local beer in a tiny, cozy atmosphere with a super friendly staff and great ales, IPAs, and summer Pilsners. 

3. Crescent Bar at the Pridwin

81 Shore Rd, Shelter Island, NY 11964

(631) 749-0476

With its stunning interiors and a sophisticated yet playful vintage camp vibe, Crescent Bar at the Pridwin Hotel is a perfect après-beach spot. Featuring magnificent water-views, this restaurant and bar offers indoor seating that spills out to the deck. True to Pridwin tradition, it also serves classic Long Island food and drink with a focus on high-quality ingredients from local farms and makers. It’s also a great place to scope the fashion scene that descends on Shelter Island during the summer.

If entertainment is your thing, the bar offers everything from bebop jazz to classic rock hits. The Pridwin also hosts a regular roster of live entertainment to underscore your evening. It’s OK if cocktails aren’t your thing. Order a mocktail like the Mango Mule, with honey, mango puree, lime juice, ginger beer, and cucumber. There’s also the Citrus Fizz with seedlip, marmalade cordial, and sparkling water. Crescent Bar is also just a quick walk or bike ride from Seven on Shelter Island.

4. Vine Street Cafe

41 S Ferry Rd, Shelter Island, NY 11964

(631) 749-3210

Vine Street Cafe, a bar in Shelter Island

While it’s not considered one of Shelter Island bars, it’s a restaurant with a cozy bar, so we’ll count it. Vine Street Cafe is the iconic eatery that is arguably one of the top restaurants in all of the Hamptons. With high-end, local fare, there’s a reason it’s always packed. From pasta, to steak, to the beloved french fries, it’s got the perfect food to pair with any cocktail. Sidle up to the bar and have a wonderful night. If you plan on imbibing, we’ll help arrange a Shelter Island Taxi for you.

5. Shipwreck at Salt

63 S Menantic Rd, Shelter Island, NY 11964

(631) 749-5535

Shipwreck at Salt is one of the most popular Shelter Island bars

When is a bar more than a bar? When it’s a boat. Shipwreck at Salt is a boat-meets-bar next to Salt, a marina-side eatery. Built in the 1930’s, this twin mast vessel roamed New England and was later used in the Great South Bay harvesting oysters and clams. Once retired, the team sunk it into their patio and stocked it with a beer keg cooler as well as a full bar. Its offerings include everything from Dark and Stormies to Whale Killers, while patrons take in the view of West Neck Harbor. It’s also available for private parties. 

If you get hungry over the course of your stay, stop by Salt. It’s a great dockside restaurant offering inside and outside dining. The menu includes fresh seafood and salads as well as interesting appetizers, soups, entrees and desserts.

6. The Tavern at The Chequit 

23 Grand Ave, Shelter Island Heights, NY 11965

(631) 749-0018

Now under new ownership, The Chequit is a stalwart hotel right in the center of the historic Shelter Island Heights district. It recently saw the opening of its new Tavern bar and grill. Like its name suggests, it’s a historically-inspired tavern. You’d expect to find hearty offerings on the menu like burgers, oysters and fresh fish, but the stand out is its wood-paneled bar that offers everything from inventive drinks to wines by the class. You can catch the game from one of its TV screens. Or you can take your cocktail outside and sit by one of its many firepits. It’s the perfect bike ride from Seven on Shelter Island, past the beautiful old homes that make our island so special.

7. The Flying Goat 

26 Sunnyside Ave, Shelter Island Heights, NY 11965

(631) 749-5404

The Flying Goat, a historic bar and golf club in Shelter Island

LocaLocated at the Shelter Island Country Club, and practically across the street from Seven on Shelter Island, this 120 year old restaurant is one of our favorites on Shelter Island. The club itself was originally founded in 1901 as a private golf club for Shelter Island Heights property owners who came to spend their summers on Shelter Island. It opened to the public in 1942 and has been hosting locals and tourists alike ever since. As for the bar and restaurant, it offers a beautiful and historic place to sit and enjoy a cool beverage after finishing 18 holes, all from one of the highest points on Shelter Island. Come for the club sandwiches, stay for local beers, wines, cocktails, and mocktails best sipped on a covered porch taking in the view.

8. White Oak Wine Garden

2 Manwaring Rd, Shelter Island, NY 11964

(631) 749-5814

The only thing better than enjoying wine, is enjoying wine in a beautiful garden. That was the idea when winemaker Tom Spotten of Lenz Winery partnered with Kristian Clark. The result? White Oark Wines, a laid-back, elegant spot on Shelter Island where patrons come to sip rose in a stunning outdoor garden. There’s also a tasting room featuring boutique wine by local winemakers as well as an eclectic mix of plants. While it doesn’t offer anything other than wine, and thus isn’t a typical “bar” per se, it’s one of those most delightful spots to iThe only thing better than enjoying wine, is enjoying wine in a beautiful garden. That was theThe only thing better than enjoying wine, is enjoying wine in a beautiful garden. That was the idea when winemaker Tom Spotten of Lenz Winery partnered with Kristian Clark. The result? White Oark Wines, a laid-back, elegant spot on Shelter Island where patrons come to sip rose in a stunning outdoor garden. There’s also a tasting room featuring boutique wine by local winemakers as well as an eclectic mix of plants. While it doesn’t offer anything other than wine, and thus isn’t a typical “bar” per se, it’s one of those most delightful spots to imbibe on Shelter Island, and just a quick bike ride away.

9. Léon 1909

29 W Neck Rd, Shelter Island Heights, NY 11965

(631) 749-9123

While also not typically on the list of Shelter Island bars, this hip new restaurant just down the street from Seven on Shelter Island has a lovely patio on which to sip a cocktail. Valerie Mnuchin and her father Robert Mnuchin debuted Léon in the summer of 2022. It’s named after Valerie’s paternal grandfather as an homage to his romantic European adventures and love for seaside destinations. Léon is an inviting homage to the past with warm, French and Italian fare. Beverage highlights include the Monsieur Fleming, with vodka, gin, lillet, dry vermouth and orange bitters. We’re also partial to the Sale e Sangue, with vodka, blood orange, lemon and a salt rim. You can also order any cocktail as a mocktail version.


Which bar should I visit to get a splashy “Hamptons experience?”

If you’re going for a fun scene, we recommend Sunset Beach. Parking can be difficult during the day, so make sure you read all permit signage at the beach across the street, otherwise you can park in the lot next door. If you’re looking for a late night, this Shelter Island bar’s unofficial closing time can be as late as 2am. Remember, Seven on Shelter Island is just a short walk away so there’s really no need to drive.

Are any Shelter Island bars and restaurants family friendly?

With children in tow, head to Shipwreck at Salt. There’s often live music during sunset with young kids dancing up front. Or sometimes the bar puts out giant beanbag games or oversized jenga. It’s a good time young and old.

If we’re coming from the North Fork, what time can we stay at a Shelter Island bar or restaurant until?

Whether you’re crossing the North or South Ferry, you’ll want to note ferry cut-off times. The last boat heading south to North Haven departs at 1:45am. The last boat heading north to Greenport leaves at 11:45pm outside of summer, and 12:45 pm from Memorial Day to Labor Day.

What’s the minimum age required for entry at a Shelter Island bar?

Like the rest of the United States, the proper drinking age on Shelter Island is 21. However, because most Shelter Island bars are also restaurants, you might find patrons under age as well as even families. But you can be sure that if you try to order a drink, you will be carded.

Are there taxi services?

Yes, we don’t condone drinking and driving on Shelter Island (or anywhere, for that matter). There are numerous taxi services listed below. We’ll help you schedule a taxi in advance or help you get your car the next day if you decide to leave it. You can also ask any restaurant host or manager throughout the island to help arrange one for you, as well.

Shelter Island Taxi

(631) 210-6677

Classy Cab Transportation Service

(631) 276-7071

Greenport Cab Service

(631) 748-2536


Whatever you’re in the mood for, you’ll find a great night out at Shelter Island bars. While the Hamptons may boast its own unique form of nightlife, our version is laid back cool, much like the island itself. Just stay safe, and remember to never drink and drive.

Shelter Island Golf – Top 9 Picks for Golfers

Shelter Island golf courses are some of the most beautiful courses on Long Island. Whether you’re a novice or pro, you can bet on having a great day playing golf on Shelter Island. But you have to know where to go.

While there’s no shortage of golf on Shelter Island, some clubs are private while others are open to the public. If you’re thinking about swinging some clubs at a golf course on or near Shelter Island, the Hamptons, or North Fork, follow along as we bring you the official Shelter Island golf guide. We’re rounding up the best Shelter Island golf and golf on Long Island. 

Read on as break down the details around Shelter Island golf courses, Shelter Island country clubs and all golf throughout Long Island. You’ll know where to go, when to play, and which courses offer the best golf. Get your clubs ready. Golf is one of the best ways to experience Shelter Island.

Where to Play Golf On Shelter Island

Shelter Island golf courses span two different courses. One is a public course and one is a private course. On a public course, you can simply sign up for a tee time, pay for your golf, and rent clubs and a cart. It’s an easy, no-strings-attached way to play golf. Conversely, at a private course, or country club, you must apply to be a member. You’ll interview with various members or committees and have other members endorse you. Then, upon admittance, you pay a membership fee and annual fees that allow you to access the golf course and other social offerings and amenities.

While it’s more expensive to join a country club, access does allow some benefits. Namely, you can play golf nearly anytime you want, as the number of golfers is more limited. You also get added benefits like social outings, onsite amenities, and a more communal, club-like feel. The golf course might be better tended given it’s private. If you’re deciding which Shelter Island golf course to play and you’re not a member, you are relegated to the public course. You can also work with golf instructors and take lessons at a country club. Country clubs offer more services, like caddies, luxurious facilities and tournaments throughout the season.

Discover the top golf clubs on Shelter Island: Seven On Shelter has listed the top 8 choices!

The Top 8 Golf Clubs In and Around Shelter Island

1. Gardiners Bay Country Club

Shelter Island’s only private country club, Gardiners Bay Country Club, was established in 1896. It’s one of the finest places to play golf on Long Island. Members enjoy a challenging 18 hole, par 70 course. They also have golf and social events for the entire family and a renowned Junior Golf School. There’s a newly renovated clubhouse offering fine and casual dining. If members want to host events, there’s a beautiful venue for a wedding, anniversary celebration or party. The club boasts some of the best water views on the East End and offers a total country club experience. Set on some of the most private, tranquil grounds of Shelter Island, this club is located right near some of the best hiking spots on the island with beautiful views at every turn.

2. Shelter Island Country Club

Known affectionately as “Goat Hill,” Shelter Island Country Club is a historic, nine-hole public golf course. It was established in 1901 and is listed on the National Register of Historic Places. The venue spans over 2,500 yards of hilly terrain. The club is also situated on one of the highest points on the island. You can see Peconic Bay and Dering Harbor from nearly any vantage point. You’re also right near Crescent Beach and some of the more private beaches on the island. You can warm up before your round at the driving range. Golf carts, pull cards, and clubs are available for rent. 

SICC membership rates start at $500 and go up to $1,052 for a family. Membership fees for singles, couples, families, and junior golfers are among the most affordable on the East End. Other amenities available at SICC include the clubhouse, which is perfect for formal celebrations and meetings. There’s also Flying Goat restaurant, which is a lowkey bar-like eatery with sweeping views of Shelter Island. You’re also very close to Sunset Beach, 18 Bay, and other Shelter Island restaurants. For junior golfers, there’s a junior golf program for kids aged 7-16 years old. 

3. East Hampton Golf Club

Hop on the South Ferry and head to the Hamptons for some Long Island golf. East Hampton Golf Club is a golf club in Amagansett situated on former farmland owned by a local East Hampton family. It’s considered one of the best golf courses in New York. The 18-hole layout was designed by world renowned golf course architects Ben Crenshaw and Bill Coore. The course offers a challenging and contrasting mix of holes played on inland links and parkland style natural contours. The greens have been called a hidden gem by many visiting golf professionals and writers.

Prior to EHGC’s opening in June 2000, the idea of turning the 126 acre parcel of land into a golf course had been contemplated for 50 years. Pete Bistrian owned and farmed a portion of the land for decades, but envisioned the possibility of building a golf course on his property. In 1978 the Bistrian family broke ground on a nine hole golf course that Bistrian was instrumental in designing. The course existed for nearly 20 years before the family members decided to contact golf course architects and create an 18 hole course. 

With 250 members, EHGC has been awarded the prestigious “platinum club designation” as a top 50 golf club in the country. The award is voted on by a panel of experts including industry leaders, owners and managers. In addition, EHGC boasts a 20,000 square foot clubhouse opened to members and guests. The exterior design features cedar shingles and river stone while the interior provides a contemporary design.

One of most exclusive shelter island golf course on Long Island is the Maidstone Club

5. Maidstone Club

The Maidstone Club is considered the most exclusive, elite golf course on Long Island. It was named one of’s 40 best places to golf in New York. It’s named after East Hampton’s original name, Maidstone, named after Maidstone in England. It was founded as a 7-hole course in 1894 and expanded to eighteen holes in 1899. The club was the summer retreat of New York City’s most wealthy and socially connected families. The beautiful course and clubhouse offers sweeping views of the Atlantic Ocean. Many consider playing there as an experience of a lifetime. 

The Maidstone Club offers AAA golf, tennis, four-star dining, a family oriented beach club with children’s activities. There are professional golf, tennis, and swimming lessons. You can also rent a cabana on the private beach. Willie Dunn laid out the first course in 1894. It was but a rudimentary seven-hole layout. Seth Raynor drew up re-design plans in 1921. Then in 1924 Willie Park, Jr. and his brother Jack designed the 80-acre Gardiner Peninsula addition. The expansion resulted in the club having two 18-hole courses, but this was reduced to the current 27-hole layout. 

6. North Fork Country Club

Are you looking for more Shelter Island golf? Take the ferry to the North Fork. North Fork Country Club is a private golf and country club in the heart of the North Fork. It’s surrounded by water, green space, and the fabulous wineries of the North Fork. If you’re on the North Fork, it’s a great place to play Long Island golf. The golf at NFCC offers competitive and social events for the club’s professional and leisure players.

There’s a Full Swing and Short Game practice facility, 18 and nine hole ladies league with weekly play, and tournaments along with clinics during the summer. There are also weekly men’s groups with mixed formats throughout the season, as well as a junior golf program that offers advanced instruction. You can sign your kids up for camps throughout the summer, junior championship, as well as an interclub team. You can also find  member-guest events, mixed couples events, and championships.

7. Pine Hills Golf and Country Club

Long Island golf clubs are often private, which means you can’t play unless you’re a member. But, there are some public courses just a stone’s throw from Shelter Island. Situated in the Pine Barrens region near Manorville on the North Fork, Pine Hills Golf and Country Club is delicately tucked away in what is practically a nature preserve. The luscious fairways and greens are surrounded by stunning, tall pines that guide you through the 165 acres and over 7,000 yards of playing area.

If you’re craving some Shelter Island golf opportunities, this course is right for you. It’s a well-maintained public course that gives players the private country club feel. You can book a private corporate outing or take friends and family on a relaxing excursion. Take a private lesson with a pro or practice all year with their chipping area and putting green. There is also a full bar and restaurant open to the public as well as golf cart rentals. You’ll have an enjoyable Long Island golf experience at Pine Hills.

Best Golf outings and Tournaments Club on Shelter Island

8. Rock Hill Golf Club

The Rock Hill Golf Club is another beautiful public course located in Manorville on the North Fork. Like Pine Hills, this club is famous for group outings and tournaments. There are shotgun outings and first tee events where tee times can be booked by groups of 16 people or more. You can create personalized tournament-style play with co-workers or other types of parties. Rock Hill also comes equipped with a high-end golf shop, driving range, and a teaching studio. There is also a restaurant available with full catering service. It’s fabulous for accommodating large groups but also pampers small parties and individuals.

If you want to improve your swing, a top-tier instructor runs the golf academy at the Long Island golf club. He is ranked as one of America’s top 50 golf teachers. The course is entirely open to the public, and costs around $50 for a round with walking, depending on the season. Anyone can pay this nominal fee to set up a tee time. For those who may find themselves frequenting this course on a more regular basis, Rock Hill offers a variety of membership packages.

9. Montauk Downs

Montauk Downs is probably the best public golf club in the Hamptons. New York State residents may qualify for half-priced green fees and other perks. It’s a challenging yet entertaining course that offers the most seasoned golfer the beauty of the game in a beautiful setting. Located Inside an incredible state park, this course feels completely isolated along the eastern shores of Long Island. Golfers are sure to enjoy this beautifully remote place to play. Players contend with the thickly wooded areas, natural ponds, and the winds from nearby Lake Montauk and the Atlantic Ocean. If you’re spending time on Shelter Island, this Long Island golf course is for you.


If you’re looking to play some Shelter Island golf, you’ll need to know where you can play. Whether public or private, Long Island golf courses are the best in the world. You’ll have a great time and improve your stroke by getting out on the course

Wine Tasting Experience – 9 Wine Tours and Tastings on Long Island

Looking for an unforgettable wine tasting experience? Hop aboard the North or South Ferry and start a wine tasting Long Island afternoon. From tours and tastings to food pairings and the best barrel rooms, Long Island offers the best wines in the world. They’re also a quick ride from Seven on Shelter Island. Here’s everything you need to know.

A wine tasting experience is the perfect way to spend a day on Long Island’s East End. The vineyards on the North Fork create some of the most beautiful wines available anywhere. These wineries love opening their doors for tours and tastings, guided tours and wine club memberships. Many consider the North Fork the Napa Valley of the East Coast. Plus, it’s a can’t miss activity that’ll get you outdoors. It’s a great excuse to drink wine during the day. What’s not to love about that? 

If you think a wine tasting experience is the perfect activity to add to your Shelter Island agenda, look no further. Read on as we round up the best wine tasting Long Island so you can get planning. Just remember to arrange your designated driver in advance or rent a driver or bus for larger groups. 

With its sandy soil and moderate climate, Long Island is best known for its incredible red wines, like classic Bordeaux blends (called “Meritage” wines in the U.S.), Cabernet Sauvignon and Merlot. The ability to grow these grapes is heavily influenced by the beach topography of the Long Island Sound, Peconic Bay, and the Atlantic Ocean.

The North Fork of Long Island contains the most vineyards. Sandwiched between the Long Island Sound to the north and the Peconic Bay to the south, this wine tasting Long Island region is home to the majority of wineries on the East End. It covers 158 square miles, which includes the peninsula from Riverhead to Orient Point, Robins and Shelter Islands.

What to know about wineries and vineyards on Long Island

  • The North Fork of Long Island is home to 37 wineries and 3,000 acres of planted vineyards. This region is the best wine tasting Long Island.
  • The largest winery on Long Island is Pindar Vineyards, which spans more than 500 scenic acres. This vineyard grows 17 varieties of grapes, molding them into over 23 varietals and proprietary blends. Pindar produces 70,000 cases of wine a year.
  • Cutchogue’s Hargrave Vineyard was Long Island’s first official vineyard. Its success led to a proliferation of vineyards. It was also responsible for preserving the farmland and the bucolic nature of the North Fork. The family later sold the winery in 1999 to the Borghese Family.
Dinner with wine tasting experience in Long Island

The price of a wine tasting Long Island tour can vary greatly. It depends on your choice of transportation, wineries, and special experiences, tours and tastings. Food pairings or private events also factor in. In general, you can expect each tasting to cost anywhere from $15 per person all the way to $95 per person. A tour company might arrange your transportation and access to about six or seven wineries throughout your day. If you choose to drive and arrange the tastings yourself, the price will be more accessible.

The best wine tasting Long Island wineries welcome drop-in tastings and don’t require a reservation, however this very much depends upon the purpose and size of your party. Are you looking for a special experience like a private tour? Are you coming in with a large party? If you are doing a wine tasting Long Island tour to coincide with a special event, start your planning process at least one year in advance.

Wine Tour FAQs

What is the difference between a winery and a vineyard? 

A vineyard is the land where grapevines are planted, whereas wineries refer to the place where the grapes are turned into wine. Often, you’ll find a winery at a vineyard, so if you’re visiting, you’ll be able to enjoy both aspects of the wine making process.

What’s so special about Long Island wineries?

New York is the third largest wine growing region in the United States. Dubbed the “Napa Valley” of the East Coast, wine tasting Long Island NY is considered the premier area in the state for wines. It produces over 500,000 cases of wine annually. This is due to the climate of Long Island, which emulates the climates of France’s wine country. Thid can give you an idea of the high quality of wines that are produced in this region.

How many people visit Long Island’s wineries?

Today more than one-million people visit the nearly 40 wineries on Long Island, and enjoy tours and tastings, wine pairings, guided tours and more.

How far in advance would you recommend making reservations at a winery?

This depends upon the purpose and size of your party. If you are making reservations for a special event such as a wedding, start your planning process at least one year in advance.

How many wineries/vineyards are open to the public?

According to the Long Island Wine Council, there are 37 wineries located on Long Island. All but two of them are open to the public. Two are only available via appointments, and one will be open soon.

Which wineries host weddings or large parties?

If you’re thinking of wine tasting Long Island NY, 26 wineries are available to weddings or other large parties. Check out’s easy to use winery finder to find out which winery best suits your needs.

Are buses, limos or vans allowed to enter the vineyards?

Not all the vineyards allow buses, limos or vans, but many of them do. If they do, they may charge an added “coach fee” to your winery experience. Additionally, all wine tasting Long Island NY wineries require advance reservations with buses or limos. You should check with your winery of choice beforehand to make sure you are aware of all of the requirements.

Wine tasting event in winery

What sort of events would be suitable to hold at wineries?

Wineries are beautiful venues that offer guests a wonderful wine tasting experience in Long Island, NY. They’re a great setting to celebrate any number of events, including weddings, picnics, corporate outings, ladies day outs, general social events, birthday parties, bachelor or bachelorette parties, or bridal showers. They also make a wonderful afternoon on the North Fork.

Do you need to make reservations to visit a winery?

You do not need to necessarily make a reservation to do a wine tasting Long Island NY (unless it is one of the two wineries in Long Island that requires appointments). This is especially true for smaller parties.

Can you visit more than one winery in a day?

Yes! Many of the North Fork wineries are located close to one another. That’s why you may see a lot of Long Island Winery Tour buses throughout your wine tasting experience. These tours usually take their guests to multiple wineries in one tour. You can have a similar experience by going independently. Just pick and choose which wineries seem most appealing to you.

When is the ideal time of year to visit a Long Island Winery?

The Long Island wineries are a perfect destination all year long. However the best time to enjoy a wine tasting experience in Long Island is during springtime and autumn. Many visitors visit during the summertime simply because it’s a nice activity to do on a hot summer day.

Wineries and Vineyards on Long Island

1. Macari Vineyards Tasting Room 

150 Bergen Avenue, Mattituck, NY 11952 


This tasting room sits on the edge of a nearly 500-acre vineyard and farm in Mattituck. Located on the North Fork of Long Island, it offers a variety of wine tasting experiences for small and large groups. Each are led by a Macari Wine Educator. Tastings are available by appointment on its covered deck or in the barrel cellar, as well as private experiences in the Private Tasting Suite. Ask for a special tasting and you’ll luck out with a charcuterie board and cheese. Or pop in on a Sunday for the rosé brunch, featuring three rosé blends and bites catered by Chef Lauren Lombardi.

2. Kontokosta Winery 

825 North Road, Greenport,  NY

(631) 477-6977

Perched atop a series of sweeping bluffs overlooking the Long Island Sound, Kontokosta Winery is a unique wine tasting experience given the beauty of its surroundings. The Kontokosta family owns and manages the vineyard and farm operations on a day-to-day basis, allowing them to shepherd the vines sustainably and at their best ripeness. It boasts some of the best views in the area, and has a laid-back vibe, good wine, and indoor and outdoor open seating. You can buy by the glass or bottle or little tasting boards, and snacks are available for purchase. FYI – there’s a $5 reservation fee required, but as a token you get to keep your wine glass.

Two men tasting red wine in Long Island

3. Pindar Vineyards 

37645 NY-25 

Peconic, NY 11958 

(631) 734-6200

An icon of the East End, Pindar Vineyards features award-winning wines inspired by founder Dr. Herodotus “Dan” Damianos. He helped create the winemaking industry on Long Island in the early 1980’s. 41 years later, Pindar Vineyards is one of Long Island’s best-known wine producers. It encompasses more than 500 scenic acres and 17 varieties of grapes crafted into 23 varietals and proprietary blends. Pindar produces 70,000 cases of wine a year, making it the largest vineyard on Long Island. Be sure to stop in on a weekend for live music. 

4. Wölffer Estate Vineyard 

139 Sagg Road 

Sagaponack, NY 11962 

(631) 537-5106

For a “scene-and-be-seen” experience, Wölffer Estate is the go-to vineyard in the Hamptons. There, you’ll find a luxe wine tasting experience. On a Friday, it comes alive with singles, couples and young families. Everyone’s sipping blends outside and taking in the beauty of the East End. Founded by Christian Wölffer in 1988, Wölffer Estate spans 175 acres in Sagaponack. It produces some of the most premium, distinctive wines, ciders and spirits. We love its White Horse wines and its Summer in a Bottle, Wölffer Finca wines, ‘Pink’ Gin and a non-alcoholic Petite Rosé Verjus. Come fall, it’s all about Wölffer’s dry ciders. This flagship Hamptons hangout is perfect anytime of year.

5. Channing Daughters Winery 

1927 Scuttle Hole Road 

Bridgehampton, NY 11932 

(631) 537-7224

Also on the South Fork, this winery features six separate vineyards on its farm, each planted from 1982 to 2007. This Hamptons mainstay was the brainchild of Walter Channing. His fascination with Italianate grape varieties led him to a 28-acre plot of land in Bridgehampton. The winery is known for churning out the finest wines from over two dozen varieties. 

Channing Daughters white grapes: 

  • Chardonnay
  • Pinot Grigio
  • Tocai Friulano
  • Sauvignon Blanc
  • Muscat Ottonel
  • Malvasia
  • Gewurztraminer
  • Ribolla Gialla 
  • Pinot Bianco

Channing Daughter Red grapes: 

  • Merlot
  • Blaufränkisch
  • Dornfelder
  • Syrah
  • Cabernet Franc
  • Cabernet Sauvignon
  • Teroldego
  • Refosco 
  • Lagrein
Red wine bottles, ready to be tasted

6. Terra Vite 

250 Manor Lane 

Jamesport, NY 11947 

(631) 722-3416

This three-acre vineyard is located on one of the most picturesque roads on the North Fork on Manor Lane. With home vines set behind the winery and tasting room, they’re planted, handed-tended to and nourished by Salvatore Diliberto for over 20 years. Stop by to sample vigorous Sauvignon Blanc, Chardonnay, Cabernet Franc, Cabernet Sauvignon and Merlot varieties. If you’re lucky, you might get to sample some oysters and other scrumptious snacks like a cheese and charcuterie board. On a beautiful day, you can sit outside. 

7. Duck Walk 

231 Montauk Highway

Water Mill, NY 11976 

(631) 726-7555

Pindar Vineyards founder, Dr. Herodotus “Dan” Damianos founded this Hamptons vineyard in 1994 with his son, Alexander. House in a Chateau-style building in Water Mill, this true Hamptons landmark became home to what has quickly evolved into one of the most well-known names in Long Island wine. Duck Walk Vineyards has two locations – the flagship winery in Southampton and a newer outpost on the North Fork added in 2007. Surrounded by 30 beautiful acres of Sauvignon Blanc grape vines, Duck Walk Vineyards North is an ideal location to taste Duck Walk’s renowned wines while enjoying a Long Island wine tasting experience. 

8. Paumanok Vineyards 

1074 Main Road 

Aquebogue, NY 11931 

(631) 722-8800

Founded in 1983, this 127-acre estate is owned and operated by Ursula and Charles Massoud and their three sons. It features premium grapevines like Chardonnay, Riesling, Sauvignon Blanc, Chenin Blanc, Merlot, Cabernet Sauvignon and more. Stop by on a sunny day to sip some wine on its beautiful deck or pair its famed Festival Chardonnay with cheeses, meats and baguette as well as fresh, local oysters. If you like what you try, you can join its wine club. 

Dinner with wine tasting experience

9. Bridge Lane 

35 Cox Neck Road 

Mattituck, NY 11952 


Bridge Lane is a cool take on the winery feel. This small farm-winery on the North Fork of Long Island is the second label produced by Lieb Cellars. It’s named after the farm road adjacent to one of Lieb’s vineyards. The grapes for Bridge Lane wines are grown sustainably on Lieb’s estate vineyard and sourced from some of the best vineyard sites in New York State. The winery prides itself on cultivating unique, high-quality, dry wines made from grapes that are sustainably farmed and made at its winery. 

The wines are made in small batches, and “crafted” by a passionate team with pride in their product. Come for the wines, stay for the games of cornhole and shuffleboard. Its large outdoor patio is perfect for a hang and sip session on one of its Adirondack chairs or inside its cozy tasting room. 


If the best wine tasting Long Island experience is what you’re after, Shelter Island is the perfect jumping off point to explore the most beautiful vineyards on the East End. Contact Seven on Shelter to set up your experience.

Shelter Island Shopping – The Essential Guide

If you’re thinking about hitting up some Shelter Island shopping outposts during your stay at Seven on Shelter Island, you’re in luck. The island boasts some of the quaintest, coolest, most stylish retail offerings on the east end, and has something sure to please everyone.

The Hamptons might be known as a shopping Mecca, where the same luxury stores that you’d find on Fifth Avenue or Rodeo Drive line the town’s streets, but there’s plenty of Shelter Island shopping to be done as well. The island is home to a charming array of independent shops catering to an in-the-know clientele that craves goods that are authentic, one-of-a-kind, and cool. 

Read on as we count down the essential Shelter Island shopping outposts throughout the island, and why the island might just be the next retail destination in both the Nork and South forks. Whatever you’re looking for, you just might find it, or perhaps something even better.

8. Finlay’s Fiction

Book lovers, rejoice. Shelter Island has its own independent bookstore that specializes in the newest fiction and non-fiction works, from bestsellers to literary ingenues, new writers, memoirs and stunning books to show off on your coffee table. They also have a lovely children’s book section and YA offerings. Every book in the store was hand-picked and carefully chosen by the owner, Finley Shaw as well as her husband, Patrick and her four children, who are often found at the store either behind the register. It’s the perfect spot for a rainy day peruse, or really any day. 

7. Black Cat Books

During your shopping in Shelter Island, you can drop at Black Cat Books
Black Cat Books

Since 1996 this vintage bookshop has been buying and selling fine used books right in the heart of Shelter Island. You can browse over 20,000 fine and used titles in all subject matters in an inviting, relaxed atmosphere. Black Cat Books is the place to discover something new or to chase down that first edition tome you never thought you’d find. While the selection might feel endless, the owner and staff know exactly what’s available and where to direct you, whether you’re eyeing the latest mystery novel or a biography to dive into on the beach. Black Cat Books is essentially a bookstore lover’s dream!

6. Marika’s 

Marika’s is an authentic gem offering highly sought-after, on-trend and unique furniture, lighting and decorative pieces. Some consider the shop a professional decorators’ secret weapon, with a stellar collection of mid-century items, especially if you’re open to digging around for treasures. The shop is run by Shelter Island local Marika Kaasik, who’s passionate about finding a home for each one of her eclectic pieces.

5. Shelter Island Pharmacy

Shelter Island Pharmacy is one of the top shopping spots of Shelter Island
Shelter Island Pharmacy

Whether you’re in need of some sunblock, antibiotics, or a gigantic breakfast, the Shelter Island Heights Pharmacy is a must-stop for all of your essential needs. Situated at the perch of the historic Heights district, this local haunt is serving up everything you might want for a long weekend at the beach or an afternoon hike, coupled with the freshest pancakes, eggs, home fries and even a few milkshakes later in the afternoon to cool you down. Seeing as it’s an actual pharmacy, the town center spot also boasts a selection of personal care items and services so you can get your shopping done and enjoy a meal, too.

4. RAM Design 

This design forward shop in the middle of Shelter Island Heights was conceived by designer and retailer Cristina Peffer as a unique retail experience featuring collaborations with a handful of Peffer’s lifelong design icons. This past summer she hosted designer Alfredo Paredes, a native of Shelter Island who launched his contemporary furniture line at the store. Think tufted slipper chairs and sofas, low-slung coffee tables, minimal beds and chic ottomans. Other collaborations include Robin Rice Gallery and Rogers + Goffigon Textiles – the latter of whom produces some of the finest quality textiles in the world. 

3. Marie Eiffel Market & Cafe

Our Shelter Island Shopping Guide recommends Marie Eiffel Market & Cafe
Marie Eiffel Market & Cafe

While this top-tier French cafe is primarily known for its show-stopping fare – think amazing breakfasts, baked goods, prepared goods and frozen food – it also has some beautiful jarred salad dressings, gifting items and adorable dining or snacking sets for sale that exude a certain Je Ne Sais Quois. But if instant gratification is what you’re after, you’ll find everyone from locals tourists to weekenders clamoring for warm baguettes, pain au chocolat or tart tatin. The cafe also makes wonderful sandwiches and fresh market fare for your beach picnic. We love its freshly roasted vegetables and salads.

2. Cornucopia Gift Shop

This lovely gift shop has everything you could possibly need, even items you’ve never thought to get but are certainly glad you did. From gifts and souvenirs, to decorations for the holidays, to the little tchotchkes that will make your loved ones smile, it’s a delightful stop on the Shelter Island shopping path. Pick up a sweet smelling candle or a cute knick knack for your favorite kiddos. Cornucopia is as quaint as the island itself. Don’t forget to say hello to the owner, Mary-Ann, who’s as charming as her shop.

1. Bliss’ Department Store

“If they don’t have it, you likely don’t need it” is how one Shelter Island native would describe this Shelter Island shopping mainstay. Quite literally, it has everything you could possibly want or need, from bed linens to sand toys to Shelter Island summer-ware. Come clearance time, it also boasts a nice selection of beach apparel, like swimsuits, shorts and tee-shirts, and the sunglass and hat collection can’t be beat. If you forgot anything on your Shelter Island shopping list, or just looking to peruse the local offerings, this store can’t be beat.

The Top 5 Items To Buy On Shelter Island

  1. Beach items from the Shelter Island Height Pharmacy. From basic sand toys to water guns to beach paddle ball, you’ll find everything you need for an amazing day in the sun – sunscreen included. 
  1. One-of-a-kind furniture from RAM Design. Whether you’re in the market for something new or just perusing, it’s worth the trouble to get these unique, design-forward pieces off the island to love at home. Our choices? A stunning Alfredo Paredes king-sized bed. If you’re not currently furnishing, pick up little accents like candle sticks or throw pillows to get the same contemporary vibe.
  1. Shelter Island Swag from Bliss’ Department Store. If you didn’t get the Shelter Island sweatshirt, were you even here? Show some pride for your home away from home with some logo’d tees, tanks, baseball hats and more. It’s one Shelter Island shopping grab you’ll need on your list.
  1. A page-turner from Finlay’s Fiction. Dive into the latest John Grisham or rediscover romance with a steamy novel all at this Shelter Island shopping favorite. There’s literally nothing better to do at the beach than bury yourself in a brand-new book. 
  1. Prepared Food From Marie Eiffel Market & Cafe. Nothing says “I love you” or “thank you” like one of Marie Eiffel’s frozen pizzas or other prepared goods. Trust us, with a few key items from this French purveyor, you’ll definitely win best hostess-gift at the barbecue.

While they may lack the luxury appeal of other east end towns, Shelter Island shopping haunts have style all their own. Discover everything from vintage items to rare book finds to the perfectly curated selection of housewares, and all without the attitude. Stop along the way for a bite at one of our fantastic restaurants. It’s no wonder people love shopping on Shelter Island. We know you will, too. 

Shelter Island Hiking – Family & Dog-Friendly Hiking Spots

If you plan to do some Shelter Island hiking or scenic walking, you’ll have wonderful options on the island. Not only is Shelter Island an incredible beach town, but it also houses some of the most beautiful trails on the entire East End.

Yes, Shelter Island is a true hiker’s paradise. For one, it’s completely stunning from every vantage point. It also possesses acres of natural wonders, like miles of coastline, picturesque creeks, as well as woodlands and fields with native species, all deserving of a true hiker’s journey (not to mention some amazing photos!) Beyond classic trails it also offers wide open spaces and preserved lands that are dog-friendly and hiking appropriate, too.

Most trails on Shelter Island are dog-friendly with the exception of Mashomack Preserve*. Visit the Shelter Island Animal Control website for more information about the rules and regulations about permitted areas, including:

  • All dogs are required to be licensed.
  • Dogs are prohibited on Crescent Beach, Wades Beach and Shell Beach between Memorial Day and Labor Day. Dogs are allowed at some Town landings.
  • Dogs must be leashed or under immediate and reasonable control of their owners.
  • No noise disturbances due to excessive barking.

Read on as we share some of the best Shelter Island hiking spots around the island. We’re bringing you the most beautiful trails that locals love, and we think you will, too.

*The hero photograph of Mashomack Preserve in this article is by Doug Young. See more of Doug’s photography in “10 Shelter Island Restaurants to Try During Your Stay” article here.

Enjoy Picturesque Shelter Island Hiking at Mashomack Preserve


The “Jewel Of The Peconic,” this massive preserve borders 11 miles of pure coastline and is widely considered one of the richest habitats in the entire Northeast. It’s of little wonder, then, why tourists and locals flock to this vast woodland for a proper Shelter Island hike. Covering over 2,350 acres, Mashomack features interlacing tidal creeks, beautiful oak woodlands, sweeping, prairie-esque fields, freshwater marshes and underwater habitats. There are up to seven color-coded trail maps ranging in length and difficulty, so there’s something for everyone, including coastal and bluff trails as well as prime wildlife viewing. Be sure to check out the visitor’s center prior to your hike to discover more about the natural elements that make up the East End.

Mashomack Preserve
79 S Ferry Rd, Shelter Island, NY 11964
(631) 749-1001

Old Nursery Woodlands Preserve


This  24.37-acre property is practically hidden in plain sight, even though it’s the geographical center of the Island. It runs along the back of many homes, stores and other structures along St. Mary’s Road near North Ferry Road. Bring your pup and meander through its meadow, virgin forest and overgrown nursery stock. The backstory is that Old Nursery Woodlands is actually part of the 1,000 acres that George Havens purchased from Nathaniel Sylvester II in 1700, and it passed to his son William Havens and to others. According to a 1909 map, its principal owners were Scudder Smith and T. M. Haisey and it passed through others thereafter. 

Access on St. Mary’s Road near North Ferry Road

Turkem’s Rest Trail


Dating back hundreds of years, this nearly six-acre property on South Midway Road is bordered by Fresh Pond to the North and Dickerson Creek to the South. About 30 percent of the property features tidal wetlands with spartina grass and native vegetation. The other portion is woods with wild cherry, oak and black locust trees. The land dates back to 500 to 1500 A.D. when a community of Native Americans from the Algonkian-speaking clan called Manhassets, lived on the shores of the Pond. You can access the preserve from Midway Road by following a circular trail. Bring your binoculars to spot migratory geese, blue herons, snow egrets and cormorants. Halfway through the trail, you’ll happen upon the largest body of freshwater on Shelter Island, Fresh Pond.

60 S Midway Rd, Shelter Island, NY 11964

Bunker City County Park


After a 23-year battle between the town of Shelter Island and Hay Beach’s developers, this 35-acre pristine tract of land was purchased by Suffolk County in 1993. Bring your dog and walk along the varied flora and fauna, including protected species such as Eastern Prickly Pear Cactus, Red Cedar plus numerous other wildflowers, shrubs and grasses. Bunker City County Park is also a nesting area for Piping Plover and features 42 acres of coastal preserve marked by red cedars and native grasses and shrubs. Access this preserve via Menhaden Lane off Gardiners Bay Drive. You’ll need a resident permit if going by car. The beach is great for walks and exploring. At night it is one of the best places for stargazing as well.

Enter at Menhaden Lane off Gardiners Bay Drive

Coecles Harbor Marine Trail


OK so it’s not a traditional Shelter Island hike per se, but if you break out your paddleboard or kayak, you can embark on a five-mile marine trail that runs along the shoreline of salty marshes filled with fiddler crabs below and osprey nests above. Think of it like a nature walk on water, where following a loop around Taylor’s Island, you’ll come across the Smith-Taylor Cabin, which serves as a landmark for boaters navigating these waters. Built by New York City magnate S. Gregory Taylor at the turn of the 20th century, the one-room log cabin was later deeded to Shelter Island Town and is now enjoyed by the public. It’s the perfect spot for a picnic before hitting the water again.

18 Hudson Ave, Shelter Island, NY 11964
(631) 749-0700

Ram Island


This quiet yet stunning enclave is perfect for catching some quality Shelter Island hiking, but it’s a quiet trail where you’ll likely have the entire area to yourself. Find your path at the Menhaden Lane parking lot (remember to have your Shelter Island Town Beach sticker) and head southeast to a peaceful 42 acres of beach scrub on your trail.

Continue along this pebbly beach, where you’ll snag ocean views from all sides, and head southeast until you reach a road that leads to Little Ram Island. From there, you’ll get sweeping views of Gardiner’s Bay, the Atlantic Ocean and all the spectacular beauty this island offers. You’ll approach Ram’s Head Inn on your right as you follow Ram Island Drive and loop around for about two more miles.

Watch for Bald Eagles at Sylvester Manor


Bald Eagle | Sylvester Manor

With its 225 acres awash with gardens, farm fields and wooded trails, Sylvester Manor is a lovely way to take in some Shelter Island hiking. This farm dates back to the 17th century and features paths behind the property’s manor house that leads to a burial site believed to house the remains of 200 people who were slaves or indentured servants. 

Follow the short trail to farm fields and the marshy area of Gardiner’s Creek, commonly known as the former site of Native American camps prior to European settlements. You might catch a deer or bald eagle so keep those binoculars handy.

80 N Ferry Rd, Shelter Island, NY 11964

Shelter Island Hiking at Sachem’s Woods


Locals love Sachem’s Woods, a one-mile loop located in the middle of the island. It’s quiet, lesser known than some of the other Shelter Island trails and are beloved for their lowkey quality and quiet beauty. Access the trail from North Midway Road near the intersection of Bowditch Road. Just know that this Shelter Island hiking spot doesn’t have bathrooms, garbage cans or parking. So anything you take in must be taken out.

Take a Detour at Arshamomaque Pond Preserve


OK so this is a bit of a detour from proper Shelter Island hiking, but just a ferry ride to the North Fork will bring you into the town of Greenport, which houses this part of the Long Island Pine Barrens Maritime Reserve. This unique complex is one of the most valuable coastal and marine ecosystems in the nation and centers on the Peconic Bays, which is a federally designated National Estuary. It’s got rich wildlife in its woodlands, open meadows, ponds and tidal wetlands and has over 2,200 feet of shoreline frontage on the pond itself.

Upon arrival, head over to Osprey Overlook, a short trail that’ll give you an opportunity to watch ospreys as they patrol the skies in search of fish. You can spot several nests around the pond as well as ducks, herons, egrets and ibis. Remember to stay on the designated trails and dogs must be leashed.

Arshamomaque Pond Preserve
920 Chapel Ln, Greenport, NY 11944

Whether you’re looking for an all day adventure or a low key walk with friends, Shelter Island hiking trails have something for everyone. You can easily spend your time amidst the trees, animals and the beautiful flora and fauna that inhabit the island and embark on journeys whose one time inhabitants date back hundreds of years. There’s so much to discover on a hike through Shelter Island. Just remember to bring your sunblock, stay hydrated and always check for ticks.

*Disclaimer: Visit the Shelter Island Animal Control website for more information about the rules and regulations about permitted areas, including: All dogs are required to be licensed, dogs are prohibited on Crescent Beach, Wades Beach and Shell Beach between Memorial Day and Labor Day. Dogs are allowed at some Town landings. Dogs must be leashed or under immediate and reasonable control of their owners. No noise disturbances due to excessive barking.

Weekend Getaways from NYC – Top 10 Places to Go

All you have to do is hop in the car or on the train to discover a variety of weekend getaways from NYC. Whether you’re a culture seeker, outdoor enthusiast, or history buff, the neighboring regions of New York offer something for everyone. From picture perfect beaches to Revolutionary War sites, to the country’s top-rated art institutions, you’ll find exceptional ways to spend a weekend outside of NYC. Below, we’re counting down the top 10 weekend getaways from NYC so that you can plan your next mini vacation away.

New York can often feel like a lot. There’s the traffic, the noise and the massive amounts of people at every turn. Sometimes, the best thing about living in the city is getting out of the city – especially when there are so many amazing destinations to travel to just a short car, train or bus ride away. Read on as we count them down.

Top 10 Weekend Getaways from NYC 

1. Shelter Island, New York 

2. Beacon, New York

3. Lexington, Massachusetts 

4. Hartford, Connecticut 

5. Cape May, New Jersey 

6. Manchester, New Hampshire 

7. Burlington, Vermont 

8. Hershey, Pennsylvania 

9. Woodstock, New York 

10. Alexandria, Virginia 

weekend getaways from nyc to shelter island new york
Shelter Island | Doug Young

1. Enjoy a Weekend Getaway from NYC in Shelter Island, New York

All it takes is 100 miles east on the Long Island Expressway to feel like you’re in another world entirely. Just over two hours from New York City, this charming island is situated perfectly between the North and South forks and contains all of the beauty of the Hamptons without the attitude or traffic. Our go-to hotel is Seven on Shelter Island, the island’s premier luxury bed and breakfast with an outdoor pool, incredible curation of art and the finest attention to detail, from the picnic baskets at breakfast to the fabulous room decor. Enjoy activities like Crescent, Shell and Wade’s Beach, have a fun, sceney brunch at Sunset Beach, take a nature hike in Mashomack Preserve, or catch some live music at Shipwreck bar in the boatyard of the marina-side restaurant, Salt. Visit Shelter Island in the summer for peak Shelter Island beach experience, but secretly, the fall might be the most beautiful time with all of the foliage taking place.

2. Take in the Arts in Beacon, New York

Just two hours north of New York City, this Hudson Valley town has it all. We’re talking lovely scenic views, cultural offerings, and amazing restaurants. To mingle with the artsy crowd, visit Dia Beacon, a massive modern art museum. For a more adventurous itinerary, hike Breakneck Ridge, a tough mountain with a four mile trail. You can also visit Bannerman Castle, a landmark castle on the Hudson River, or walk through town and enjoy a wealth of cool eateries, galleries and local shops. For lodging, we prefer a stay at Rushmore Estate, a genteel B&B in a Spanish colonial mansion on a 50-acre estate and just 8 miles from the Storm King Art Center. You can also opt for The Roundhouse, featuring upscale, sleek rooms in an industrial-chic hotel with farm-to-table dining and a riverside patio. Buttermilk Falls Inn and Spa features high-end rooms in a luxury inn that offers a spa and  tennis court, plus an elegant restaurant. If you’re deciding when to visit Beacon, you can’t really go wrong. But, we’re partial to the fall for optimal leaf-peeping vibes.

3. Discover American History in Lexington, Massachusetts

Just over three hours from New York City, one of our favorite weekend getaways from NYC is a town outside of Boston. Lexington is perfect for everyone from history buffs to professional imbibers, boasting historic taverns and relics dating back to revolutionary times. We recommend hitting up the Minuteman Commuter bikeway, a paved trail for cycling and jogging. The Scottish Rite Masonic Museum and Library is perfect for discovering American history artifacts, and the Lexington Common National Historic Site is a revolutionary war battle green that puts you back into the Revolutionary War era. Soak up the New England fall with an October visit or come in the spring or summer for warmer temperatures. The best places to stay include the boutique bed and breakfast, The Inn at Hastings Park. Hipsters can opt for the trendier Verb Hotel, an authentic rock n’ roll experience with an outdoor pool right near Fenway Park, and Concord’s Colonial Inn for true Americana vibes.

lexington massachusetts getaways from nyc

4. Arts and Culture in Hartford, Connecticut 

A mere 2.5 hours outside New York, the Connecticut capitol offers plenty to do, namely visiting the Mark Twain House and Museum where the writer wrote his classics. For culture junkees, there’s also Wadsworth Athenium Museum of Art, the Connecticut Science Center and the Connecticut Historical Society Museum. If you’re deciding where to stay, opt for a room at the trendy Goodwin Hotel, a timeless, classic property with a modern flair. There’s also the Delamar Hotel, a full-service luxury experience with on-site amenities, or the Silas W. Robbins House, a boutique bed and breakfast on the most beautiful piece of land. Like most New England towns, visit Hartford in the spring, summer or Autumn to experience the outdoors. If you opt to visit during the winter, plan your days indoors. 

5. Stay at Some of the Best Hotels in Cape May, New Jersey 

This charming New Jersey beach town is three hours south of New York City, close to the New Jersey / Pennsylvania border. It’s known for grand Victorian houses like the Emlen Physick Estate, which is now a museum with interiors preserved from its heyday. We love hitting up all the shops and restaurants lining Washington Street Mall, three pedestrian blocks where families often stroll after their days spent at the beach. But Cape May offers plenty more to do than frolic in the sea (though you’re welcome to it, too). Visit the Cape May Lighthouse, a historic landmark with a museum, or the Wildwood boardwalk for games, snacks and a signature Jersey shore experience, and the Historic Cold Spring Village, a living history village dedicated to life in the first years of American independence. The best hotels include The Star Inn, a laidback property with ocean views, the posh Beauclairee’s Bed and Breakfast Inn, and the Grand Hotel of Cape May, an upscale oceanfront resort with a pool. If you can’t tell already, we highly recommend this town in summer.

weekend getaways from nyc to burlington vermont

6. Take in the Views in Manchester, Vermont

Just 3.5 hours from New York City, this idyllic town in southern Vermont embodies the true New England experience. Start your weekend off by visiting Hildene, the estate of Abraham Lincoln’s son Robert. It’s a Georgian Revival mansion complete with gardens and a farm. The American Museum of Fly Fishing is a fun stop-by, featuring rods, flies and angling-related art. Nearby, the Southern Vermont Arts Center has varied exhibits, as well as a sculpture garden and performance space, plus sprawling grounds with forest paths. Just west of town, you’ll find a trail that climbs all the way up Mount Equinox. Stay at the Inn at Manchester, a historic hotel with pool and pub, or Wilburton Inn, an elegant hotel with a sculpture garden. The Equinox Resort and Spa is great for a full resort-like experience. Travel there in fall, spring or summer for outdoor beauty or come in the winter for peak ski season.

7. Play in the Snow in Burlington, Vermont

Another quintessential Vermont town, Burlington is a 5.5 hour journey making it one of the further weekend getaways from NYC. This journey takes you to the northwestern part of this snowy state, on the eastern shore of Lake Champlain, south of the Canadian border. Take in some local treasures downtown, where shops and restaurants line the pedestrianized Church Street Marketplace. North of downtown, the Ethan Allen Homestead Museum is a former home of the Revolutionary War hero. For history buffs, the vast Shelburne Museum, south of the city, houses American folk and decorative art in a collection of historic buildings. For cozy New England vibes, stay at Willard Street Inn, featuring traditional rooms in an 1881 mansion. There’s also Made INN Vermont, an urban chic bed and breakfast and Lang House on Main Street, a stately mansion with a quaint inn. Visit in the fall for beautiful foliage or summer to go lake-hopping. Winter will have you cold, but you can ski at nearby local mountains.

8. Sweets and More in Hershey, Pennsylvania

Can you smell the chocolate? Just over three hours from New York near the state capital of Harrisburg, this town chronicles the life of Milton Hershey and his enormous contribution as the founder of Hershey Chocolate. There’s Hersheypark, which opened in 1907 as a modest green space but grew to include rides, attractions, a waterpark, fun chocolate-themed activities – plus a zoo! Hershey Gardens is a beautiful must-see with a stunning rose garden (Milton’s passion) as well as a butterfly house. Plus Hersheypark Stadium and Giant Center host great concerts. There’s nothing like playing at the theme park all day followed by a fun music show at night. Stay at the Hotel Hershey, a polished inn with luxe amenities, or Hershey Lodge, a family friendly hotel with an indoor waterpark. Visit in spring or summer for full floral blooms and plenty of fun at the waterpark! 

9. Take a Short Weekend Getaway from NYC to Woodstock, NY

Just two hours from New York, this small town tucked at the foot of the Catskill Mountains has been a symbol for peace, love, art, and community since the 1960’s. Today, it retains its art-forward personality, with dozens of galleries, boutiques, educational centers, spiritual centers, hiking trails, nature preserves, food, and outdoor markets. Hit some trails at Catskill Park – 700,000 acres of wilderness that spans four counties in the state. Or wander the art galleries along Tinker Street, like the Woodstock Artists Association and Museum and the Woodstock Byrdcliffe Guild. Go marketing at Mower’s Saturday Flea Market. Located just a block from the central Village Green (on Maple Lane), this small green space comes alive on weekends with vendors from all across Ulster County. They’re selling everything from vintage clothes, jewelry, and records to fresh farm produce, wood-fired pizza, and more. Plus, there’s usually live entertainment, and it’s a warm, welcoming place to visit where neighbors get together to socialize. Stay at Hotel Dylan, with retro-chic rooms with record players in a hip hotel offering an outdoor pool and Mexican restaurant. Scribner’s Catskill Lodge is a rural, contemporary hotel offering mountain views and a rustic restaurant and bar. The Graham & Co. Hotel is a laid-back inn offering design-forward rooms and an outdoor pool. Go in the spring and summer to enjoy the outdoors, or head there in the winter to ski nearby Hunter and Windham Mountains.

weekend getaways from nyc to alexandria virginia

10. Take the Whole Family to Alexandria, Virginia

Just four hours from New York City, this historic town offers easy access to the best of Washington DC sightseeing, including the United States Capitol, Lincoln Memorial, National Gallery of Art, and the Smithsonian National Museum. It’s the perfect destination for children, their grandparents, and everyone in-between. Stay at the Morrison House for an intimately luxe stay, The Ritz Carlton for a resort-like experience, or the the Lorien Hotel and Spa in the historic, waterfront district featuring Washington-era homes, King Street shopping & foodie restaurants. Time your stay with the cherry blossoms that bloom in the first week of April.

Summer 2022 is nearly over, but you can enjoy weekend getaways from NYC all year long. Our advice? Book them fast. These top destinations around the New York metro area tend to fill up quickly. So whether you’re brainstorming a trip to the beach or a hike in the woods, we recommend starting to plan for it now.

Corporate Retreat at Seven – Debra Boulanger Shares Her Experience

Debra Boulanger shares her experience hosting a corporate retreat at Seven as well as her Shelter Island Top 5.

As a native of Sag Harbor for the last 16 years, Debra Boulanger has a deep-seeded love for Shelter Island and hops the ferry whenever she can. Debra founded The Great Do-Over, a coaching organization that helps professional women navigate a new career as founders of their own businesses.

Last October Debra hosted her annual Six Figure CEO Corporate Retreat at Seven on Shelter Island, where women from her Six Figure Accelerator course stayed at Seven and enjoyed the feeling of the outdoors and tranquility of Shelter Island as they charted their paths to success. Here Debra shares her background, her love of coaching women and what makes Shelter Island so special.

corporate retreat at seven on shelter
Seven on Shelter Island Pool

Tell us about the Great Do-Over

The  Great Do-Over is a coaching and mentoring business for women leaving the corporate world and starting their own businesses as coaches, consultants, speakers or other entrepreneurs.

What led you to starting The Great Do-Over?

I had spent over 25 years in the corporate world and at one point, I was burned out. At the same time, on a personal level, I was heading for divorce, my mother’s health was failing, I had a 13-year-old son. Everything felt like it was coming into collision, and I had to reinvest myself and decided to start a coaching business after my own personal reinvention, which I called my Great Do-Over. So I named the company after that. 

What sort of services do you offer?

I support women leaders who are making the leap from corporate to entrepreneur. It’s generally three service offerings. There’s the launch lab, which is the first stop on the path. It helps answer questions about what you’re offering, like how do you package it? How do you price it? How do you get clients? That’s why we created the launch lab for women entrepreneurs. It’s a four month mentorship and mastermind program to get started and create those first revenue generating activities.

After that, my clients ask me, well how do I grow my business? How do I get new clients, speaking engagements and get on corporate stages? How do I develop an offering portfolio to handle more than one customer segment or to have a longer engagement with clients that I have? How do I increase the customer lifetime value? This is a six figure accelerator that’s one year long with women entrepreneurs who are eyeing six figure revenue growth in their business. But, whether they’re making $50,000 or earning more than six figures in their practice, this is for women who want to accelerate it, double revenue or grow revenue by a predictable six figure growth margin year over year.

The third program l launched is how to stand out in webinars. It’s helping my clients who have to create online seminars that are informative and engaging. It’s how to get new clients everytime you speak. 

Many of my clients take all three courses and end up building a good deal of momentum and attend our six-figure growth predictor corporate retreat, which I held at Seven. That was the retreat, which is part of the experience in getting women from our weekly group calls together. Once or twice a year we get together as a community to nurture ourselves as CEOs of growing businesses. It’s to stay connected to their mission, vision and values. It’s increasing our own skills and the capacity to lead an ever growing business.

What fields do most of these women come from?

Oftentimes it’s coaching and consulting in leadership coaching, like C-suite executives, or career coaching. I also do sales coaching, non-profit fundraising. There’s a broad spectrum of skills. Sometimes I’m helping people improve their speaking skills. Other times it’s a focus on specific industries, like holistic or wellness, to grow their revenues and impact. So each client’s work is based on their own mission. 

What is it about age and wisdom that can lead people to finding their next passion? Do you feel like it can only come with age?

What’s been really interesting for me is that my clients are getting younger and younger. A good portion of women I work with are in their thirties. I work with everyone from women who’ve excelled up the corporate ladder and are now rethinking their next phase, to a former Olympic figure skater who’s transitioning into an executive coach and leadership coach. I’m helping give them the skills they need in strategy, pricing, packaging, messaging and sales skills. 

What are some of the trends you see among the people you work with? What are the pin points or fear factors involved in starting over and how do you try to alleviate those?

There’s a lot of fear when they first start out. Most of my clients are successful business leaders and c-suite executives who have established success in their career, and then they’re making the leap to decide to launch a business starting from scratch. Although they have incredible skill-sets and talents developed in the corporate world, when you launch your own business, you’re also cmo, cfo, ceo. So suddenly, it’s how do I get good at sales? How do I market my services? How do I get in front of new clients? How do I speak from stages? All the other skills are a stretch, plus there’s no corporate paycheck. There’s no team supporting you to get all of your work done. You have to build a team from scratch. Hire and delegate as much as you can afford to so that it will free up time on business strategy.

Tell me about your Six Figure CEO Corporate Retreat at Seven last October….

The world was just opening up after the pandemic. I was looking for a space that would be luxurious as well as constrained and safe for clients that would also exude luxury. These are my most valuable clients. I wanted to give them a high end experience and that was everything like the environment in the decor of the house. Style is really important to me and the fact that Beth had spent so much time and effort in the design of the rooms and the overall luxury experience of her inn was really luxurious. Her attention to detail, from the sound bowls in the enclosure by the pool, to the breakfast laid out in the morning, to the art on the walls, the furniture choices. Each room was outfitted so perfectly for the experience I wanted to create for our clients. 

seven on shelter is a beautiful island bed and breakfast in new york great for corporate retreats

Why is Shelter Island so special?

The experience of stepping away from the day-to-day to go on a ferry is very symbolic. You’re leaving the mainland behind, over water, and arriving somewhere else. There’s a big exhale. It’s so beautiful and welcoming there and we were blessed with a gorgeous weekend in late October. It was 70 degrees. It was incredibly beautiful. We spent time outdoors, walking Crescent beach daily. It was a great environment for our clients to have time away in nature and to join us for meals and the programmed events we had. 

Debra’s Shelter Island Top 5: 

Salt: “This seaside is one of my favorite summertime haunts. I love the fresh seafood and being right on the harbor.” 

Mashomack Preserve: “There’s nothing quite like a walk through Mashomack anytime of year, but particularly in the autumn when all of the leaves turn. It’s the most peaceful thing. I’ve lived in Sag Harbor for 16 years, and hiking Mashomack is always such a treat.” Read more about Shelter Island hiking in our article here.

Crescent Beach: “This the beach where we walked every morning on the Six Figure CEO Retreat when staying at Seven. It’s so beautiful, especially when it’s so calm before the boats start to come in.”

Marie Eiffel Market: “A must-stop if you’re in town, Marie Eiffel has the freshest produce, most delicious baked breads and yummy grab-and-go items to take on your beach picnic. It’s no wonder it’s one of the busiest stops on the island.”

Vine Street Cafe: The most perfect and delicious setting for dinner on the island. The food is “special occasion” worthy and yet it’s so charming and relaxed – just like the rest of the island. Read more about Shelter Island Restaurants to try in our article here.

*The Debra Boulanger portrait in this article is by Alyssa Peek.

Amelia Clark on the Shelter Island Ferry and More

Amelia Clark Practically Grew Up On The Shelter Island Ferry

If there’s one person you could consider the eyes and ears of Shelter Island, it might be Amelia Clark. The college junior was raised on Shelter Island and is part of the legendary Clark family that’s run the South Ferry since the 1800’s. She and the rest of her Clark crew work hard year in and year out making sure everyone coming from the Hamptons gets on and off the island as efficiently and safely as possible. To say she and her family are the heartbeat of Shelter Island would be an understatement.

Amelia Clark | Photograph provided by Amelia Clark

When she’s not issuing tickets on the ferry, you’ll find Amelia working at Shelter Island’s most high-end restaurant 18 Bay, babysitting some local kids, and even popping her head in at Seven! So naturally, we had to find out Amelia’s top Shelter Island picks and what she loves most about this magical place. 

Tell us about your family and the Shelter Island ferry…..

I believe we are the oldest family run ferry company on the East Coast, but it’s always been our family that ran it on Shelter Island. The house I grew up in was the original ferry house, and right outside our house is where the ferries dock at night, right on the beach. 

My grandfather and his brother run the ferry together. Before that it was their dad. My dad is the scheduler for the ferry. He’s worked there ever since we’ve lived there. My mom worked on the ferry when she was pregnant with me. I started training to work there over winter break.

How did that go?

It was really fun. There’s a lot of technicality to it. When you’re charging people, you have to go by different prices, sizes, lengths, and how many people are in the car. You have to take all of that into account. So there are a few different formulas. I’ll probably have to get retrained for summer because going back to school fills my brain back up, but it’s really fun. People who work there are so nice. We’re big on having a positive attitude and always being kind to everyone. Who would want to work somewhere that’s not a positive environment? No one wants that reflected onto them.

Is there ever any friendly competition with the North Ferry service?

18 Bay | Shelter Island Restaurant | Photography by Doug Young*

I don’t think about it as competition. They take people to the North Fork and we take people to the South Fork. Typically people will go through both of us depending on where they’re going, so I don’t think of it in a competitive way. I believe the North Ferry is a corporation. They do things differently. They are advancing more technologically, for example they have scanners. We haven’t gotten there yet, but I’m not sure we feel like we need to. 

Tell us about the training process….

It’s really hands-on. When you’re training, they have a trainer with you. So first you’re walking around with him or her for a bit to see what they do. Slowly, they implement different tasks, at first you’re loading and unloading and opening the gates. Then once you have that down, it’s OK, now you’re going to go to the windows, get money and click tickets. OK that sounds like a plan. I got that down. Then you keep doing it over the course of a week, and your trainer is there to let them know if you need any help with anything. I won’t know everything right away because there’s so much to remember and recheck up on. But everyone’s so nice and so helpful about it. A lot of people come across with a commuter or resident pass, so if you know the price of a car typically then you’re fine. 

What’s life on Shelter Island like now compared to when you were growing up?

Shelter Island Ferry | Photograph by Doug Young

I feel like it’s changed a little bit. The North Fork is getting “hamptonized,” so to speak. I can almost see it in some cases and feel it coming to us, just the people and the changing of businesses and the new businesses that come around in the summer. It’s like when I used to go to Sag Harbour as a child, it was very similar to Shelter Island. They were two small towns, but the vibe has gotten different as I’ve gotten older and it feels like it’s spreading through to here, too. I think we have a doctrine that we can’t have chains or fast food, but I can feel it spreading in different ways.  

What was it like to grow up on Shelter Island?

Shelter Island Ferry Captain | Photograph by Doug Young

I loved it. It can be complicated in some ways. There were small classes, I mean 23 kids were in my graduating class senior year. But it’s like a little family inside a bigger family. The population all year ‘round is not very big and you’re surrounded by the same kids your whole life. So their parents are your pseudo parents and they check up on you and support you. You always see your teachers around. You see them in the summer on the beach. But you can have amazing experiences because the classes are so small. You get to go on a Schooner trip in seventh grade. We went to Disney World in eighth grade. We get to go see Broadway shows fairly regularly. We also just feel like we have a lot of support that makes itself available to us.

Do you think you’ll stay on Shelter Island?

As nice as I think it would be to raise kids on Shelter Island, at some point I’d like to go away for a bit. I plan to summer here myself, and I’ll probably move back when I’m older, but I’ve always enjoyed big cities and really crowded places. I actually like background noise when I sleep. Shelter Island is eerily quiet at night for most of the year, so that’s made it difficult for me to sleep. My parents crack up. They used to take me to music festivals in New Orleans and Austin, and the noise would always help me go to bed. That was not the case for them. I’ve always felt comfortable with more people. I’m going to try to embrace that more.

What do you love most about Shelter Island?

The sense of community. It’s always been the best thing. I’ve always felt taken care of. Everyone looks out for you. I was so involved at school so I was my cousins’ TA in their art classes. When my cousin was in kindergarten, I was a TA in that class, too. And just even the involvement of babysitting. I babysat so many of those kids I’m a junior in college, so these kids I babysat are getting into middle school and high school, and I’ve watched them, all of them. All their parents know me.

Amelia Clark with family and friends at Shelter Island’s South Ferry | Photograph provided by Amelia Clark

Amelia’s Shelter Island picks:

Maria’s: “I love Maria’s. That’s always been my favorite place to go if we wanted to get food after school. The food is great, and in the summer it’s awesome to sit outside. Maria is a sweetheart. I went to high school with both of her kids. She always talks about her kids when I come in, and asks me how I’m doing. She always checks up on me.

The beaches: “Shelter island has the best beaches. Crescent Beach is awesome. The sand is less rocky. If you get there earlier, it’s really great. And everywhere is so safe. Our joke is that we don’t have a key to our house. We don’t lock our car doors. The beaches are also so safe.

18 Bay:  “Jimmy is the manager and Chef Adam and Elizabeth are the sweetest people. I’ve worked there since I was 16. They’re my other family. They check up on me all the time and are so supportive. The food is so good, too, and the menu changes every week. Sometimes they let me eat there.

Greenport: “There are so many cute shops and places to eat. I really like this one little shop called Tea and Tchotchkes. They sell crystals and really cute clothes and self-help books and tarot cards. I love going in there. I’ll go once a week to stand around and get crystals and a necklace or something.

Grindstone Coffee and Donuts, Sag Harbor: This place is so good. On Shelter Island we don’t have a lot of fast food. There’s no Dunkin Donuts etc. I’m not even a big donut person, but I love going in. It’s also across the street from Whites Apothecary, which has so many nice skincare and makeup brands. I love going in and debating whether I can afford to buy anything.

Stars Cafe: I love that place so much. They’ve got the best muffins and bread every morning, especially in the summer. They also make the best breakfast wraps and sandwiches. Right door is the pharmacy, which is really the pinnacle place on Shelter Island. The milkshakes are top tier.

Read more about the top things to do in Shelter Island here.

*View more photographs by Doug Young here.

The Top 25 Things To Do in Shelter Island

There’s no shortage of things to do in Shelter Island, New York. From the gorgeous beaches to the incredible expanses of nature to some of the best culinary outposts on Long Island, Shelter Island is a gem set in the middle of the East End with plenty of activities for people of all ages. We’re giving you an overview of all the fun you could possibly have on Shelter Island, whether you’re jonesing for a perfect day at the beach, an on-water adventure or some relaxing shopping in town. Shelter Island has it all.

Perfectly situated between the North and South Forks of Long Island, Shelter Island is one of the most beautiful islands on the entire East Coast. Whether you choose to visit on a crisp fall day or in the height of summer, there are so many things to do that you can simply take your pick. The island is surrounded on three sides by the Shelter Island Sound and on the fourth side by Gardiner’s Bay. That means that outside of swimming in fabulous beaches or setting sail on the bay, you’ll do well dining at any of the island’s restaurants, as they’re always sourcing ingredients from the best farms for local produce and the freshest catch of the day.

If you come visit us at Seven on Shelter Island, you can essentially design a daily itinerary that’s perfect for you. With so many things to do in Shelter Island, it might appear overwhelming, but we’re breaking down the essential list so that you can maximize your stay and enjoy our little slice of paradise.

shelter island ny sylvestor manor
The Sylvester Manor
Salt Restarant Bar and Grill
Black Cat Books

We obviously think Shelter Island is fantastic, but why should you visit Shelter Island? Well, aside from all the things to do, you’ve got the perfect combination of quaint vibes with a strong dose of style from the nearby Hamptons. Only on Shelter Island, there are no velvet ropes or waiting lists. It’s a come as you are, picture perfect place.

*All photography in this article is by Doug Young.

The Top 25 Things to do in Shelter Island

A. Beach/Swimming/Boating:

  1. Crescent Beach
  2. Hay Beach
  3. Shell Beach
  4. Wade’s Beach
  5. Reel Point

B. Sightseeing/Hiking:

  1. Shelter Island Kayaking
  2. Mashomack Preserve
  3. Shelter Island Country Club
  4. The Sylvester Manor
  5. Bootleggers Alley

C. Indoor Activities:

  1. Finlay’s Fiction
  2. Black Cat Books
  3. Shelter Island Brewery
  4. White Oak Wine Garden
  5. Shelter Island Pilates & Barre

D. Family-Friendly:

  1. Whales Tale
  2. Wade’s Beach
  3. Peconic Water Sports
  4. Camp Quinipet
  5. HiBerry Beach Lane

E. 21+/Adult Activities:

  1. Shipwreck Bar
  2. Sunset Beach Bar
  3. The Perlman Music Program
  4. 18 Bay Bar
  5. Salt Restaurant Bar & Grill

A. Beach/Swimming/Boating:

things to do shelter island ny wades beach
Wade’s Beach
  1. Crescent Beach: Known for its magnificent sunsets and halfmoon shape, this beach is the perfect combination of family-friendly and adult-oriented. Kids will enjoy swimming in the gentle, calming waters without gigantic waves or you can all rent paddle boards together without the fear of getting lost at sea (though there is a bit of a current, so stay close to shore). For the 21 and over set, Sunset Beach is the official party spot of the island, where a DJ spins beach tracks all day and the rosé starts popping by early afternoon. Think European vibes right here on Shelter Island. As its name suggests, sunset hour is the perfect time to pull up to this beach and take in all of the magic, and spotting the yachts that pull up is an added bonus. We love how close it is to Seven, just one block away!
  2. Hay Beach: For a quieter beach experience, head to this locals-only beach
    that’s perfect for swimmers. Grab your flippers and masks for a fun snorkel
    outing or bring your pup, as this beach in particular is very dog-friendly. We
    love packing up a picnic lunch and finding a spot that’s entirely our own for a
    sublime afternoon in the sun. You might also spot a few fishermen catching the
    day’s specials.
  3. Shell Beach: This narrow stretch of beach makes for some pretty epic 360-degree views of the water. If you investigate, you’ll find trees with shells perched on the branches like Christmas ornaments. Kids will love collecting all sorts of shells that decorate the sand as well. There are gentle bay waves here, which lends it a family-friendly feel, and this beach is the perfect place to plant your umbrella and chill out for the day. It’s also quite pup-friendly as well, making it one of the most popular things to do in Shelter Island.
  4. Wade’s Beach: This popular sunning spot is where the locals descend when
    they’re seeking a day at the beach. Bring your kayak, wind surf board or paddle
    board and get out on the water and enjoy. We love this beach for its covered
    gazebo, especially when you want to picnic in the shade, as well as its super tidy
    public restrooms. If you want to be truly adventurous, get a license and go
    clamming. The local hardware store in town sells the tools and shovels you’ll
  5. Reel Point Beach on Ram Island on Shelter Island: This fragile sand peninsula
    offers a beautiful wildlife habitat at the tip of Ram Island. You’ve got a mix of
    American beach grass, seaside goldenrod and bayberry, making it a haven for
    migratory birds and butterflies, like osprey, piping plovers and Monarchs. If you’re
    a nature lover, bring your binoculars and join the fun. Just note that vehicle parking
    permits are required at all Shelter Island beaches. They go for $70 in the summer

See Ana Gambuto’s Top 5 Beaches on Shelter Island here.

B. Sightseeing/Hiking:

  1. Shelter Island Kayaking: These kayak tours are fun for the entire family and give
    you a glimpse into Shelter Island, as only experienced from the water. Head out
    with a guide or explore on your own along the breathtaking Mashomack Preserve
    or head into nearby West Neck creek.

80 Burns Rd, Shelter Island, NY 11964
(631) 749-1990

mashomac shelter island hiking
  1. Mashomack Preserve: This massive preserve covers one-third of Shelter Island and offers various trails in difficulty levels to enjoy with a group or on your own. Mind the colored markers of the trail and set out exploring. If you love to bird watch, you could catch some wonderful beauties out there, or just take a walk in the incredible meadow. Be sure to meet the guide in the museum and have a quick chat before you set out. This landmark area of Shelter Island is protected by the Nature Conservatory and is one beautiful place to visit. Please note that there are no dogs, bikes or jogging here.

79 S Ferry Rd, Shelter Island, NY 11964
(631) 749-1001

  1. Shelter Island Country Club: Also known as Goat Hill, this club right across the street from Seven is a public, nine hole golf course with reasonable rates. We love the hills throughout the club, which make for a proper golfing workout, but carts are available for rent, as are clubs. The Flying Goat Restaurant sits at the highest point of the island so you can enjoy dinner and drinks after the 18th hole and take in the beautiful view.

26 Sunnyside Ave, Shelter Island Heights, NY 11965
(631) 749-0416

  1. The Sylvester Manor: Once a Native American hunting, fishing and farming ground, this Shelter Island mainstay has been home to 11 generations of the same family since 1651. Over time it’s evolved into an organic educational farm supported by the island’s neighbors and friends and encourages community, a celebration of food, and the arts. Walk the grounds with your dog on leash and explore the stunning grounds and don’t forget to pick up some fresh fruits and vegetables at the market on site.

80 N Ferry Rd, Shelter Island, NY 11964
(631) 749-0626

  1. Bootleggers Alley: Known for the best fishing on the island (be certain to get a fishing license at Town Hall first), this small stretch of beach is the perfect spot for a long walk to Crab Creek.

Shelter Island Heights, NY 11965

C. Indoor Activities:

  1. Finlay’s Fiction: Book lovers, rejoice. Shelter Island has its own independent bookstore that specializes in the newest fiction and non-fiction works, from bestsellers to literary ingenues, new writers, memoirs and stunning books to show off on your coffee table. They also have a lovely children’s book section and YA offerings. It’s one of the most relaxing things to do on Shelter Island on a rainy day, or really any day.

8 Grand Ave, Shelter Island Heights, NY 11965
(203) 650-7616

  1. Black Cat Books: Since 1996 this vintage book shop has been buying and selling fine used books right in the heart of Shelter Island. You can browse over 20,000 fine and used titles in all subject matters in an inviting, relaxed atmosphere. Black Cat Books is the place to discover something new, or to chase down that first edition tome you never thought you’d find.

54 N Ferry Rd, Shelter Island, NY 11964
(631) 725-8654

Shelter Island Brewery
  1. Shelter Island Brewery: This craft brewery specializes in small batch brews made with local ingredients. Each brew is concocted and made by owner and brewer Jim Hull, so you know it’s as local and authentic as it gets. The brewery’s staple selection of beers are supplemented with an ever-changing selection of seasonal beers and it offers yummy snacks and board games to enjoy while you sip. Get there early to score one of the outdoor picnic tables and be prepared to chill.

55 N Ferry Rd, Shelter Island, NY 11964
(631) 749-5977

  1. White Oak Wine Garden: Made by Winemaker, Tom Spotteck of Lenz Winery in partnership with Kristian Clark, this lovely little wine garden featuring White Oak Wines specializes in a laid-back and elegant ambience in which to enjoy this classic Rosé wine. The property’s tasting room features some of the best boutique wine by Local Winemakers as well as an eclectic mix of indoor plants and outdoor gardens to explore while you imbibe.

2 Manwaring Rd, Shelter Island, NY 11964
(631) 749-5814

  1. Shelter Island Pilates & Barre: Founder Suzette Smith, is a former dancer who offers core-based workouts for people of all ages. Now with two locations, you can access a daily schedule of pilates-based and barre workouts using state-of-the-art technology or work one-on-one with a trainer.

8 Grand Ave, Shelter Island Heights, NY 11965
(631) 749-5042

D. Family- Friendly

  1. Whales Tale: This wonderful ice cream shop, arcade and mini golf emporium offers hours of fun and is one of the most exciting things to do in Shelter Island with the entire family. Whether it’s a cloudy day, after dinner or you’re just looking to switch it up from endless beach days, you can’t beat hearty scoops of Hershey’s ice cream and a fun romp through 18 holes of mind-bending mini golf. We also love its indoor fun offerings, featuring air table hockey, old school pinball games and more. Please note, Whales Tale is cash only.

3 Ram Island Rd, Shelter Island, NY 11964
(631) 749-1839

Peconic Water Sports
  1. Wade’s Beach: This family friendly beach offers tons of fun for tots and parents, alike. For kids, well what’s better than playing in the water, collecting seashells and building sand castles? Parents can hang back in their beach chairs knowing that the beach offers super calm, shallow waters without the Atlantic Ocean waves. There’s also super tidy restrooms, a covered gazebo for lunch and options to bring your own kayak and paddleboard for an added adventure.
  2. Peconic Water Sports: Looking to get out on the water with the family? The best water sports rental on the entire east end, Peconic Water Sports is the only company on Long Island that uses brand new boards, waterskis, kites, life jackets and boats each and every year. Its staff is professionally trained in not only safety but having a lot of fun. Whether you’re learning how to wakesurf or trying to progress to the next level in water skiing, its knowledgeable staff keeps it fun and educational out on the bay.

3253 Noyack Rd, Sag Harbor, NY 11963
(631) 680-0111

  1. Camp Quinipet: This nature-focused summer camp offers all the trappings of a traditional camping experience with the options of overnight camp, day camp and a sailing camp for kids. It’s the perfect opportunity for kids to learn new skills while parents can enjoy a quiet day at the beach.

99 Shore Rd, Shelter Island Heights, NY 11965
(631) 749-0430

  1. HiBerry Beach Lane: This small, quiet beach on an inlet is a bit hidden among tourist crowds, and all the better. It’s amazing for a summer stroll, where you can walk around the point towards Hay Beach Point. It’s also dog friendly and has zero crowds, even in the peak of summer.

E. 21+/Adult Activities

  1. Shipwreck Bar: This is the go-to spot on the island for live music and a frothy drink or a good old bottle of beer. Outfitted out of a real boat, this boatyard favorite is a great pre-dinner drink spot, especially if you’re dining at Salt next door, or a great destination for happy hour if you’re biking around the island.

63 S Menantic Rd, Shelter Island, NY 11964
(631) 749-5535

  1. Sunset Beach: This European-inspired swanky chic spot has everything you’ll need to enjoy a perfectly made adult beverage at one of their two bars while enjoying the sunset. You’ll want to break out your most stylish looks for this spot. The scene-and-be-seen crowd won’t disappoint.

35 Shore Rd, Shelter Island Heights, NY 11965
(631) 749-2001

The Perlman Music Program
  1. The Perlman Music Program: Get a dose of culture on the island and enjoy an evening concert over at this hidden outpost on Crescent Beach, where gifted young musicians and faculty from around the world perform under the tent each summer season.

73 Shore Rd, Shelter Island Heights, NY 11965
(212) 877-5045

  1. 18 Bay: One of the top rated restaurants on the island and throughout the Hamptons, this husband and wife team offers a special menu each night of ala carte items sourced from the finest farms and local purveyors on the East End. They also make a great cocktail.

23 N Ferry Rd, Shelter Island, NY 11964
(631) 749-0053

  1. Salt Restaurant Bar & Grill: Watch your favorite team on the large screen TV with a basket of fries and a beer on tap or take in the beauty of the boats coming in at this marina favorite. Pro-tip: it’s got one of the best lobster rolls on the island. Stop by Shipwreck Bar down the road before dinner for a pre-sunset cocktail.

63 S Menantic Rd, Shelter Island, NY 11964
(631) 749-5535

As you can tell, there’s plenty of things to do in Shelter Island. The joy lies in discovering what you want to do when. Our recommendation? Try and do it all, and then come back for more.