Top 10 Things to do on Shelter Island

Top 10 things to do on Shelter Island:


Arriving by ferry is a great segue to adventure. Shelter lsland, a mere 27 square miles, intimate, quirky and beyond pretty. Located just 90 miles east of NYC allows for quick getaways with a whole lot of salt air. Vast tracts of protected wetlands, and nearly one-third of the island is preserved in a wild state. There are countless activities and places to see.


Here are our top 10 favorite activities and favorite spots:


  1. Island BeachesShelter Island beach – With some 20 miles of coastline and a variety of beaches ranging from sandy beaches with lifeguards to rustic spots that offer beauty and seclusion, we would have to list our number one activity to explore our island beaches, 6 unique beaches to be exact. Plenty of options to stroll, collect shells, sunbath and swim in the clean bay waters that surround us. Our staff favorite, Crescent Beach (aka. Sunset Beach) is just a 5 minute walk from the hotel and the keeps it namesake.
  1. Mashamock Preserve Mashamock Preserve on Shelter IslandA 2000-acre preserve, considered one of the richest habitats in the Northeast. Fantastic hiking trails range from 1.5 to 11 miles, allow exploration of wildlife in a natural setting for all skill levels
  1. Taylors Island – accessible only by water, via the Coecle’s Harbor Marine Water Trail this is a wonderful stop for kayakers. Travel via Kayak and explore and picnic on the Island and its historic Smith-Taylor Cabin, built around 1900. Enjoy a serene paddling adventure exploring the unique natural beauty of Shelter Island’s calm, protected creeks and harbors. No experience is needed. Shelter Island Kayak Tours.


  1. Paddle boarding – Whether your a veteran paddler, ready to double down on your workout with a paddle yoga class, an explorer, or want to Paddle Boarding on Shelter Islandreally learn how to paddle properly on a stand up paddle board. Venture Out is your point of contact, boards can be delivered to any location to allow a close up exploration of marine life in the clear waterways, creeks and inlets without disturbing their habitats.
  2. Sylvester Manor – Sylvester Manor Educational Farm is a 243-acre historic plantation and nonprofit educational farm on Shelter Island, NY, engaging all ages in farm-based programs. A visit to the farm stand in season for organic homegrown produce and artisan delights is not to be missed. Of interest there is the windmill, burial grounds and archaeological sites.
  3. Havens’ House Museum – Open to the public, the museum is a fascinating glimpse of early Shelter Island. Managed by the Shelter Island Historical Society, The museum also features the Havens Store with books by local authors, unique locally-made merchandise, nautical maps and much more. Home to our seasonal farmers market, antique car shows, children’s time travelers program.Fresh flowers from Sylvester Farmstand
  4. Shopping – Whether it’s antiques, souvenirs, art or fashion, Shelter Island can fulfill your retail therapy. Like many of our activities on the Island, many boutiques or gallery’s are open seasonally. For the fashion conscious, Marie Eifflel Boutique, offers international acclaimed and imported designers plus a custom line to take men and women from beach to urban chic. And for the iconic Shelter Island souvenir t-shirt, keepsake or a free fudge sample a visit to Bliss’ Department Store will never disappoint.

    Menu at The Pharmacy on Shelter Island

    Menu at The Pharmacy

  5. Shelter Island Heights Pharmacy – Breakfast at this iconic soda shop will take you back to a simpler time. Belly up to the counter and join the locals for coffee, and a classic griddle top breakfast. Best kept secret the, pharmacy milkshake!
  6. Shelter Island Country Club – The Shelter Island Country Club, also known, as “Goat Hill” is a public nine-hole golf course. The course covers 2,512 yards of widely varying terrain. Situated on one the highest points on the island, gives scenic views of the Peconic Bay & Dering Harbor.It’s also a great place to enjoy a cold drink or have a bite to eat
  7. Petanque at Shelter Island House – Gather round for good old fashioned fun in our outdoor lit courts. Grab a glass of rose after a delicious dinner at the Tavern at Shelter Island House and head out to the lawn to meet friends and to relax under the stars with some friendly competition. Petanque is extremely simple, just like horseshoes. There’s a target, and you have to get as close to it as possible. What makes it so appealing is that you can be way ahead for a while, yet lose a second later – nothing is decided until the last player plays the very last boule. Age, strength or speed are not important.Outdoor court at Shelter Island bed and breakfast


Discover why so many seek Shelter Island for their favorite getaway year round! Call to inquire about rates and packages at Shelter Island House, 631-749-1633.