Best Things to Do on Shelter Island, NY: Nature, Shopping, Dining and More
Shelter Island is not the type of destination where you need to rush from one major attraction to another. Part of its appeal is having time to slow down, enjoy the scenery and decide what you feel like doing that day.
We have been visiting Shelter Island almost every summer since 2013, and we continue to find new places to explore while returning to the activities that have become part of our Island traditions. Some days are spent hiking or kayaking, while others involve little more than visiting a local shop, eating ice cream and finding a quiet place near the water.
Whether you are planning a day trip or staying for an extended weekend, these are some of our favorite things to do on Shelter Island, NY.
Planning a Shelter Island Getaway?
Hi! Danielle here and this article is part of our Shelter Island travel series.
Explore our guides to the best breakfast spots, beaches and things to do during your visit.
Hike Through Mashomack Preserve
One of the best ways to experience the natural side of Shelter Island is by spending a morning at Mashomack Preserve.
The preserve includes woodlands, fields, freshwater marshes, tidal creeks and miles of shoreline. Its trail system offers several options, making it possible to enjoy a shorter nature walk or dedicate several hours to exploring.
Mashomack is managed by The Nature Conservancy and is often referred to as the “Jewel of the Peconic” because of its diverse habitats and protected coastline.
As you walk, look for ospreys, turtles, deer and other wildlife. The experience changes depending on the trail, season and time of day. Some areas pass through shaded woods, while others open to marshes and scenic water views.
This is one activity we recommend doing earlier in the morning, especially during the summer. The temperatures are usually more comfortable, wildlife may be more active and you will still have the rest of the day available for the beach or lunch.
Wear comfortable walking shoes, apply insect repellent and bring water. It is also important to remain on the marked trails and follow the preserve’s current visitor guidelines.
Best for: Nature walks, birdwatching, photography and a peaceful morning outdoors
Address: 79 South Ferry Road, Shelter Island, NY 11964
Official website:
Explore Mashomack Preserve
Play Mini Golf at Whale’s Tale
For a lighthearted activity that does not require much planning, spend an hour playing miniature golf at Shelter Island Whale’s Tale.
The 18-hole miniature golf course follows the story of a friendly whale making its way to Shelter Island. It is a casual, old-fashioned summer activity that works well for families, couples or anyone looking to take a break from the beach.
The course is not overly complicated, which is part of the fun. You can play at your own pace and enjoy a little friendly competition without turning it into an all-day outing. Turn in your putter at the end and get an ice cream cone!
Whale’s Tale recently was renovated by new owners. They now have a photo booth that prints your photo for free (such a cute little souvenir!), a fire pit, an espresso bar, and hot snack foods late into the night (which is a rare find on Shelter Island.) Whale's Tale is a good activity for the late afternoon or early evening.
Hours are seasonal and may change depending on the weather, so check before heading over.
Best for: Families, date nights, groups and a break from the beach
Address: 3 Ram Island Rd, Shelter Island, NY 11964
Stop for Ice Cream at the Tuck Shop
No summer weekend on Shelter Island feels complete without at least one ice cream stop.
The Tuck Shop has been an Island staple since 1980 and is the kind of classic neighborhood ice cream shop that becomes part of your vacation routine. It offers hard ice cream, soft serve, sundaes, shakes and take-home treats.
After spending the afternoon at the beach, we love stopping for a cone and taking our time deciding between all the flavors. It is a simple activity, but sometimes those small vacation traditions become the things you remember most.
There is seating available, or you can take your ice cream with you and continue exploring. Summer evenings can become busy, but standing in line with other beachgoers is part of the experience. Most times we get our ice cream to go and head down to Crescent beach to watch the sunset.
Best for: An after-beach treat, families and a classic summer evening
Address: 75 North Menantic Road, Shelter Island, NY 11964
Visit the Havens Farmers’ Market
If your Shelter Island visit includes a Saturday morning like ours did, add the Havens Farmers’ Market to your itinerary.
Held on the grounds of the Shelter Island History Center, the seasonal market brings together local growers, food producers, artists, makers and Island organizations. Visitors can browse fresh produce, baked goods, bread, seafood, cheese, flowers, jewelry, artwork and handcrafted items.
One of our favorite parts of the market is that it feels like a community gathering rather than simply a place to shop. There may be live folk music toward the back of the grounds, and visitors have an opportunity to speak directly with the farmers and makers behind the products.
Walk through the entire market before deciding what to purchase. Some of the vendors and musicians are located farther back, and it is easy to miss them if you only visit the first few tents.
The market is scheduled for Saturdays from late May (usually around Memorial Day weekend) through September / Labor Day weekend, from 9:00 a.m. to 12:30 p.m. It is held rain or shine, and admission is free.
Best for: Local food, handmade gifts, meeting Island businesses and a relaxed Saturday morning
Location: Shelter Island History Center
Official website:
Visit the Havens Farmers’ Market
Shop at the Sylvester Manor Farmstand
Another favorite stop for locally grown food is the Sylvester Manor Farmstand, located at Windmill Field.
The farmstand carries seasonal produce grown at Sylvester Manor, along with eggs, flowers, pork and prepared foods. You may also find bread, cheese, chocolate, fruit, candles, body products and other goods from farms and small businesses around the East End. If you are also looking for souvenirs or unique home goods, this is another great place to check out.
This is a great place to pick up fruit for the beach, vegetables to bring home or something prepared to enjoy during your stay. The selection changes throughout the season, which means every visit may offer something different.
Do not rush in and out without taking a moment to appreciate the surrounding property and historic windmill.
Sylvester Manor is a working educational farm and historic site with seasonal walking trails, cultural programs and events. The grounds are generally open seasonally from March through October, while certain buildings may have restricted access.
The farmstand currently lists daily hours from 9:00 a.m. to 5:00 p.m., but it is still wise to confirm before visiting.
Best for: Local produce, picnic supplies, flowers and gifts made on the East End
Address: 21 Manwaring Road, Shelter Island, NY 11964
Official website:
Visit the Sylvester Manor Farmstand
Go Kayaking or Paddleboarding
Shelter Island is surrounded by protected bays, harbors and creeks, making kayaking one of the best ways to see the Island from a different perspective.
Depending on where you launch, you may paddle past beaches, marshlands, docks and quiet residential shorelines. The experience can be as relaxing or active as you want it to be. We enjoy taking our time, staying close to the shoreline and appreciating views that cannot be seen from the road.
Visitors who do not have their own equipment can rent single or double kayaks and paddleboards from Venture Out. The company operates a walk-up location at Crescent Beach and also offers delivery to other locations around Shelter Island.
Morning is often a good time to paddle before the beaches become busier. Always check the weather and wind conditions, wear a properly fitted life jacket and stay within an area appropriate for your experience level.
Best for: Couples, families with older children, nature lovers and active mornings
Official website:
Visit Venture Out Shelter Island
Spend the Day Relaxing at the Beach
Of course, one of the best things to do on Shelter Island is nothing at all.
Some of our favorite days involve packing a cooler, bringing a good book and spending several hours beside the water. Shelter Island offers everything from lively, supervised bathing beaches to small town landings where you can sit quietly and watch the boats.
Crescent Beach is a good choice when you want lifeguards, restrooms and more activity. Wade’s Beach offers a family-friendly atmosphere and a shaded pavilion, while places such as Menhaden Lane, Bootlegger’s Alley and Shell Beach provide quieter surroundings.
Most public beach parking locations require a seasonal permit, so make sure you understand the current rules before leaving your vehicle.
We created a separate guide comparing the different shorelines, facilities and views:
Read next:
Best Beaches on Shelter Island, NY
Browse Shelter Island’s Local Shops
Shelter Island is not filled with large shopping centers or national chains—and that is part of what makes shopping here enjoyable.
You will find a changing collection of bookstores, vintage shops, home décor stores, art studios, clothing boutiques and businesses carrying Island-themed gifts.
Some of our favorites:
- Bliss Department Store
- Shelter Island Hardware
- King Andrew Cheese
- Shelter Island Craft Brewery
- Elli's Country Store
- Black Cat Books
- Kanela Handmade
- Shelter Island Flowers
- Dworkin & Daughter
- Marika's Eclectic Boutique
View current Shelter Island Chamber of Commerce business listings in the link below.
Because many shops are independently owned and seasonally operated, their hours may be limited. We like to keep our plans flexible and stop whenever we see an interesting shop open.
Shopping locally is also an easy way to support the community beyond hotels and restaurants. Whether you purchase a book, piece of jewelry, vintage record or small souvenir, the item becomes a reminder of your time on the Island.
Best for: Rainy afternoons, locally made gifts, books, art and one-of-a-kind finds
Business directory:
Explore Shelter Island’s local shops
What Are the Best Things to Do on Shelter Island?
The best Shelter Island itinerary is usually a combination of activity and relaxation.
You might begin the morning hiking at Mashomack Preserve, stop at the Sylvester Manor Farmstand and then spend the afternoon at Wade’s Beach. Another day could include kayaking, browsing local shops, playing miniature golf and finishing with dinner near the water.
Try not to schedule every hour. Shelter Island is a place where a quick stop at a farmstand, an unplanned drive down a waterfront road or an extra hour at the beach can become the best part of the day.
Even after visiting for more than a decade, we still find something new each summer. That is one of the many reasons Shelter Island remains one of our favorite places to relax and unwind.
Continue Exploring Shelter Island
Continue planning your trip with the rest of our Shelter Island travel series:
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