things to do on shelter island

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.