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A Local’s Guide to Shelter Island

By August 8, 2018No Comments

A Local’s Guide to Shelter Island


Shelter Island offers a taste of New England close to New York City. Sandwiched between Long Island’s North and South forks, this 8,000-acre hamlet is a 10-minute ferry ride from Greenport or Sag Harbor.

“As soon as the boat backs away from the dock, however, you can feel a sense of calm descend as the view of the Hamptons fades across the water,” says Corcoran agent and long time Shelter Island resident Peter McCracken.

Rebecca Shafer, a Corcoran agent who made the move to Shelter Island a few years ago after decades of owning in the Hamptons, agrees: “You smile as soon as you get on the ferry knowing you’re heading back to this oasis of calm.”

We invited McCracken and Shafer to share their insider tips—and must-visit spots—for this hidden-in-plain-sight gem.

What to Do: Boats, Beaches, Bikes and Hikes

You come to Shelter Island for the water, and there are many pristine sandy beaches from which to choose. McCracken likes to visit tranquil Shell Beach, which occupies a small peninsula that faces the West Neck Harbor on one side and the bay on the other. Crescent Beach is his choice for a popular bay beach; it has a lifeguard and public restrooms, plus its calm waters make it perfect for paddle-boarding.

For a family spot, he recommends Wade Beach, where there are always lots of kids and a lifeguard. Shafer’s favorites includes Silver Beach on the Peconic or Hay Beach for its stunning views of Gardiner’s Bay. (Note: All beaches require a town permit to park.)

Beyond the beach, the island is easy to explore by bicycle, McCracken says. if you haven’t brought your own, you can rent one at Piccozzi’s Bike Shop. And Shafer recommends the green jewel of Mashomack Nature Preserve for its walking trails that traverse the wildlife-filled park.

Both agents describe Shelter Island as a boater’s paradise, with everything from rowboats to yachts plying the waves. McCracken encourages new sailors to get their sea legs. Shelter Island Yacht Club is a private club that offers sailing programs for non-members, and Camp Quinepetruns sailing programs for kids all summer.

Where to Stay

Shelter Island offers a range of accommodations. The Chequit (be sure to pronounce it CHEE-quit), opened in the 1800s and has undergone a recent renovation, but is still known for its warm hospitality. The Ram’s Head Inn, tucked into the quiet Eastern reaches of the island, has an emerald lawn that rolls down to the water and is a popular spot for weddings. Shelter Island House offers eight plush rooms and a central location; its Italian dining destination, Caci, is on both agents’ lists — the gnocchi Bolognese is “to die for,” says McCracken. For proximity to the nightlife scene, Sunset Beach, with a hip design by hotelier Andre Balazs, is the spot.

Where to Shop

The historic Heights neighborhood offers a charming downtown with unique shops, including Bliss Department Store, which stocks everything you need for a Shelter Island getaway, including beach towels, topsiders, T-shirts and housewares. Another destination shop is Dabney Lee for fabulous hostess gifts and monogrammed items.

For gourmet bites and delicious picnic provisions, Shafer hits Marie Eiffel Market as soon as she arrives on the North Ferry for everything from charcuterie to Nutella beignets. “I thank her everyday for being on this island,” Shafer says.

Where to Eat

In the summer, dining outside at Sunset Beach restaurant—with its fabulous people watching, outdoor dining and sunset views—makes it seem as if you’ve been transported to the south of France. “It feels a bit like Saint-Tropez,” McCracker says. Ordering the Frose (a frozen blend of rosé, rum, and strawberries) on a hot summer day is a must, as well as dishes like veal Milanese and baked clams.

For the perfect seafood meal, Shafer heads to SALT, noting that you can dock your boat right at the casual seaside spot before digging into coastal favorites like lobster rolls, grilled tuna and mussels. Also here is the Shipwreck Bar, an old wooden boat converted into a drinks destination that welcomes all ages to listen to live music and enjoy the cool breezes.

The dining scene reflects the appeal of Shelter Island to its many fans. “It offers a small town beach charm,” Shafer says, “but with sophisticated and interesting places and people.”

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