Things to Do on Shelter Island

Your Guide to Shelter Island Activities

Shelter Island is a hidden gem tucked between the North and South Forks of Long Island, offering a refreshing mix of outdoor adventure, cultural experiences, and laid-back island living. Whether you are visiting for a weekend getaway or spending the entire summer, there is no shortage of things to do on this peaceful 8,000-acre island surrounded by Peconic Bay and Gardiners Bay.

Water Sports & Boating

With water on every side, Shelter Island is a paradise for anyone who loves being on the water. Kayaking and paddleboarding are among the most popular activities, with several outfitters offering rentals right from the beach. Paddle through the calm waters of West Neck Harbor, explore the shoreline of Mashomack Preserve by kayak, or launch from Crescent Beach for a sunset paddle across the bay. Sailing is deeply woven into the island culture — from casual daysails on Gardiners Bay to private charters that take you past Montauk and the Hamptons. If fishing is your thing, the waters around Shelter Island offer excellent striped bass, bluefish, and fluke throughout the season.

Golf & Recreation

The Shelter Island Country Club features a scenic 9-hole course with water views that has been welcoming golfers for over 120 years. It is one of the most charming courses on the East End and a favorite among both locals and visitors. Beyond golf, the island offers tennis courts, a public playground, and plenty of quiet roads perfect for cycling. Rent a bike and explore at your own pace — the island is only about 7 miles across, making it easy to cover in an afternoon.

Nature & Hiking

Shelter Island is home to the Mashomack Preserve, a 2,039-acre nature sanctuary managed by The Nature Conservancy. Often called the “Jewel of the Peconic,” Mashomack features miles of trails winding through oak woodlands, marshes, and coastline, with opportunities to spot osprey, deer, and harbor seals. For a lighter walk, stroll the village streets of Shelter Island Heights or explore the paths around Sylvester Manor, a 243-acre working farm and educational center dating back to 1651.

Horseback Riding & Family Fun

Paard Hill Stables offers horseback riding lessons and trail rides through the island scenery — a unique experience you will not find elsewhere on the East End. For family-friendly fun, do not miss the Whale Tale, a beloved local ice cream shop with mini golf that has been a Shelter Island tradition for decades. Grab a cone, play a round, and enjoy the kind of simple summer pleasure that makes this island special.

Getting Here

Shelter Island is accessible by two ferry routes. The North Ferry connects from Greenport on the North Fork, while the South Ferry connects from North Haven near Sag Harbor. Both ferries run frequently and the crossing takes just a few minutes. Check our ferry schedule for current departure times and plan your island adventure today.