August 28, 2017

Things to do, Places to Eat, and Where to Stay on Shelter Island, New York

Shelter island is a verdant, gorgeous swath of land nestled between the North and South Forks of Long Island chock-full of beautiful beaches, a nature preserve, delicious restaurants and more.

by Nicole Haddad photographer Nicole Haddad

Shelter Island Things to Do
Left to right: Stamberg Aferiat Associates' Shelter Island Pavilion, a Cubist reinterpretation of Mies van der Rohe's Barcelona Pavilion guided by Newtonian Color Theory; The Shipwreck Bar's seaside-inspired decor; Canoeing is a popular leisure activity on the island.
Shelter Island
Clockwise from top left: The Island Boatyard and Marina;
The view from the Bridge Street Volunteer Park in Shelter Island
Heights; Sunset Beach Hotel's cheerful set up on Crescent Beach.

A VERDANT ISLAND nestled between the North and South Forks of Long Island, Shelter Island is aptly named. First settled in 1652 by a sugar merchant named Nathaniel Sylvester, today, the 8000-acre island—situated about 110 miles from Manhattan—retains an old-world, low-tech charm that evokes a nostalgia for the Hamptons of bygone days. A frequent visitor over the years, designer Glenn Gissler says, "It is a place where time has stood still. It's nourishing to the spirit—the magic of Shelter Island is based on what's not there."

mashomack preserve in shelter island
Left to right: The Mashomack Preserve encompasses 12 miles of coastline; The Manhanset Chapel on North Ferry Road was built in 1890; One of Mashomack Preserve's trails.
Sunset Beach Hotel
Guests enjoy a sunny day at the Sunset Beach Hotel.

Despite a growing year-round presence of a population estimated at around 2,400, and an influx of summer visitors over the last 15 years, the sentiment continues. But surprisingly enough, for a bucolic, mostly sleepy town (excepting André Balazs' trendy Sunset Beach Hotel), with a tiny shopping district and smattering of restaurants, cultural institutions abound. The most notable, the Perlman Music Program—founded by Toby Perlman in 1994 with a world-class faculty led by Itzhak Perlman—offers musical training to string players with rare talent. There's more than enough to keep you busy, but the idyllic beaches inspire rest and relaxation. Shelter Island reflects a simpler time when hiking, bike riding, boating, board games, and reading were the most popular of American pastimes.

Sylvestor Manor Shelter Island
Left and right: A detail of a The Gatehouse, Sylvestor Manor's shop; The Sylvester Manor House, a c. 1737 Georgian house that was built over the original 1652 manor, has had many reincarnations, including as a sugar plantation and a commercial farm; Today, it is part of a nonprofit educational institution.

Shelter Island can be reached by ferry: North Ferry Co., departs from Greenport, Long Island, and South Ferry Company departs from North Haven, Long Island—vehicles included. Or, splurge and fly StndAIR
directly from the East River to Crescent Beach in only 45 minutes.

Shelter Island Things to dO havens market
Clockwise from left: Dabney Lee on Bridge Street; Strawberries from the Havens' Farmers' Market, held every Saturday through September 2nd; White Oak Farm & Gardens offers unique plants and landscape services.

Hike one of the Mashomack Preserve's trails. The nearly 2,100-acre habitat makes up an estimated third of the island and is replete with tidal creeks, woodlands, fields, and freshwater marshes. Tour the 243- acre Sylvester Manor Educational Farm—an historic 1652 plantation that is now a nonprofit educational farm. Visit the Havens' Farmers' Market on Saturdays for local produce, flowers, pies, and more. Watch the sun set at Sunset Beach Hotel's happening restaurant and bar. Be a beach bum: Shell and Crescent Beach are quite beautiful. Drive through Shelter Island Heights, where the Victorian homes date back to the 1800s. Enjoy Sunday Jazz Night at the Ram's Head Inn.

Ram's Head inn on Shelter Island
Left: Ram's Head Inn; The Hampton Hopper offers transportation around the Hamptons.

André Balazs' pricey-yet-hip beachfront Sunset Beach Hotel offers twenty guest rooms with private sundecks. The Pridwin Hotel is a charming 90-year-old resort located on Crescent Beach with a pool overlooking the bay. The 10-acre site includes family-friendly cottages, a tennis club, lounge, and restaurant. The Chequit, located in an 1872 building, was given a shabby chic renovation and claims one of the best restaurants in town, Red Maple. A bit off the beaten path, the Ram's Head Inn is an alluring gem.

Biking and Canoing Shelter Island
Left and right: Kayak Island Tours offers serene paddling adventure tours through the island's protected creeks and harbors; A bicycle rider enjoys the lush landscape.
Shelter Island Pharmacy
The Shelter Island Pharmacy has an old-school soda fountain.

Alison and Keith Bavaro's laid-back waterfront restaurant, SALT, opened in 2012. Follow dinner with a cocktail and live music at their nearby sister joint, The Shipwreck Bar—an authentic 39-foot schooner reconfigured as an outdoor bar. 18 Bay Restaurant, set in a c. 1893 building, offers an Italian-inspired menu that changes weekly. Vine Street Café is a big draw with a seasonal menu sourced from local farmers, fishermen, and winemakers. Lose the diet: Sit at the Shelter Island Heights Pharmacy's old school lunch counter and enjoy a decadent breakfast sandwich and hashbrowns.

The Shelter Island Historical Society is adding a two-million-dollar History Center set for completion in January 2018. The Society operates Havens House, the island's only museum.

The Stand Mercantile in Shelter Island
The Stand Mercantile.
Dering Harbor in Shelter Island
Dering Harbor in Shelter Island.

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