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.