Shelter Island Marinas – Our 3 Favorite Spots To Get Boating

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Shelter Island marinas are a boater’s paradise, especially for sailors! With stunning views, calm waters, and abundant marine life, the island thrives on boating as one of the island’s most popular activities. Whether you’re a seasoned sailor or a novice boater, there’s something for everyone at Shelter Island marinas. Here, we’ll explore the main marinas and Shelter Island harbors – their locations and services, including boat rentals and charters.

There are three beautiful Shelter Island marinas and harbors that offer a full range of services. They include Dering Harbor, Island Boat Yard on West Neck Harbor and Coecles Harbor Marina & Boatyard.  

Amenities at these marinas and harbors include fueling, pump-out, and electrical hookups – with more services offered depending on the marina. Additionally, there are several options for boat rentals and charters on the island. 

Check Out the Beach Goers

On your boat, you can also peer out at Crescent Beach, just down the block from Seven on Shelter Island. Or check out all the beach-goers at Wades Beach and Shell Beach. If it’s racing you’re after, there are several events and races throughout the year, including the annual Around Shelter Island Race. This event attracts sailors from all over the world. With its natural beauty, you can’t go wrong on the water and at any of our Shelter Island marinas. 

Read on as we break down these Shelter Island marinas, so that you can be prepared should you want to set sail on stunning Shelter Island. Whatever you decide, a great day awaits you at these top destinations around the island.

Shelter Island Marinas and Harbors:

Dering Harbor is a picturesque marina located on the north side of Shelter Island, it is a charming boating destination just east of Greenport.

1. Dering Harbor

Picturesque Dering Harbor is located on the north side of Shelter Island, just east of Greenport. It’s right in the middle of the charming Shelter Island Heights area, filled with cute cafes and independent shops like beach gear stores, high design boutiques, and more. The marina features 60 slips. It also offers boat accommodations for boats up to 75 feet long. The marina provides a full range of services, including fueling, pump-out, electrical hookups, and water. The Village of Dering Harbor (a short walk from Bridge Street) is an attraction in and of itself, and makes a lovely morning stroll to take in the views of the water and the beautiful wooden sailboats.  

If you’re seeking more amenities with your boating experience, Dering Harbor is home to the prestigious Shelter Island Yacht Club. However, you will need a member to invite you there, or you’ll need to be a member of one of its reciprocal yacht clubs. The Shelter Island Yacht club is one of the premier yacht clubs on the East Coast. It’s been a fixture of the community since its founding in 1886. The club offers a range of activities including sailing lessons, racing programs and social events. 

The SIYC also boasts the largest fleet of H12 wooden sailboats designed by Nathaniel Herreshoff. The club’s beautiful clubhouse looks over Dering Harbor and offers stunning views of the water. Members can also access the private marina, which includes over 100 slips and state-of-the-art facilities. The Shelter Island Yacht Club is committed to promoting the sport of sailing and community among members. 

2. The Island Boatyard Marina on West Neck Harbor

This Island Boat Yard Marina is a popular destination for boaters on Shelter Island. This full-service marina offers everything from boat storage and repair services, to fuel and dockage. The marina offers easy access to some of the best fishing, boating, and water sports in the area. The facility also has a friendly and knowledgeable staff that can assist your boating needs. Its location on Shelter Island, close to trails, hikes and more, is serene and scenic. Salt Waterfront Bar & Grill and its neighboring Shipwreck Boat Bar 

makes the Island Boat Yard Marina a perfect place to stop for lunch or dinner.  Whether you’re a captain or just starting out, the Island Boatyard is a great place to set sail.

  • Services: Full-service marina, including boat repair, maintenance, and storage, fuel dock, pump-out station, dockside electricity, water hookup, ice, showers, WiFi, marine store, and transient slips.
  • Address: 135 North Menantic Rd, Shelter Island, NY 11964
  • Website: https://www.islandboatyard.com/
The Coecles Harbor marina is a picturesque retreat for boaters seeking serene surroundings and top-notch services.

3. Coecles Harbor Marina & Boatyard

Coecles Harbor Marina is another beautiful Shelter Island marina with a good portion of its perimeter is along the Nature Conservancy’s Mashomack Preserve. Located on the southeast side of Shelter Island, and features 68 slips, with accommodations for boats up to 65 feet long. Like the other marinas, it offers a full range of services, including fueling, pump-out, and electrical hookups.  Take your dinghy ashore to enjoy dining at the historic Ram’s Head Inn.  

  • Services: Fuel dock, pump-out station, laundry facilities, showers, WiFi, dockside electricity, water hookup, dinghy dockage, transient slips, mooring rentals, marine store, marine repairs, boat rentals, and charters.
  • Address: 21 South Menantic Road, Shelter Island, NY 11964
  • Website: www.coeclesharbormarine.com

Discover the Beauty and Prestige of Shelter Island

With its stunning coastline and picturesque harbors, Shelter Island is a lovely destination for boaters. While sailing, you can see many stunning landmarks and beaches around the island or the Hamptons. Check out the historic Montauk Point lighthouse, which has been guiding sailors since 1796. Or, if you dare go even further, head towards Connecticut and New England. 

However you get out on the Shelter Island waters, you cannot go wrong. Not only is it the ideal way to spend a day, but our marinas ensure you’ll have everything you need to set sail safely and comfortably. We’ll see you on the water!

Shelter Island Hiking – Family & Dog-Friendly Hiking Spots

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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

NO DOGS ALLOWED

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

DOG-FRIENDLY

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

DOG-FRIENDLY

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

DOG-FRIENDLY

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

DOG-FRIENDLY

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

DOG-FRIENDLY

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

DOG-FRIENDLY (LEASH REQUIRED)

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

DOG-FRIENDLY

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

DOG-FRIENDLY (LEASH REQUIRED)

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

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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.

The Top 25 Things To Do in Shelter Island

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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
    require.
  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
    season.

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
https://www.kayaksi.com/

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
https://www.dec.ny.gov/outdoor/55663.html

  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
https://www.shelterislandcc.org/

  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
https://www.sylvestermanor.org/

  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
https://www.finleysfiction.com/

  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
http://blackcatbooks.com/

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
https://shelterislandcraftbrewery.com/

  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
https://www.whiteoakfarmandgardens.com/menu-1

  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
http://www.shelterislandpilates.com/

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
https://www.shelterislandwhalestale.com/

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
https://peconicwatersports.com/sag-harbor/

  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
https://www.quinipet.org/

  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
saltshelterisland.com

  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
https://sunsetbeach.fun/

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
https://www.perlmanmusicprogram.org/

  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
http://18bayrestaurant.com/

  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
saltshelterisland.com

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.