Shelter Island, nestled between the North and South Forks, is a destination for visitors looking for a variety of scenery and old-fashioned country charm not found in other parts of the East End. Accessible only by ferry, the island escapes most of the hype and bustle of the rest of the Hamptons.
Finding your way around the island is relatively easy. Route 114, the main north-south road, zigzags its way between both the North Haven and Greenport ferries. Generally speaking, if you are coming from the South Fork, Mashomack Preserve and Ram Island will be on your right; Wades and Crescent Beaches will be on your left.
According to old records, Shelter Island was known as Ahaquatawamock by the native people, the Manhansetts, who lived there when Dutch and English colonists began establishing their beachheads in
The European presence on the island began in earnest in 1651 when a group of English colonists bought the island from a Stephen Goodyear, who had been awarded it as a commission in 1642 by the Earl of Sterling. By one account, the price paid was 1,600 pounds of muscovado sugar. A second sale, after the island's Native Americans protested to colonial authorities in Connecticut, is recorded in old town records. One of the purchasers, Nathaniel Sylvester, and his wife, Grissell, started a supply farm for sugar plantations in Barbados. Sylvester's will listed 24 slaves among his possessions. Sylvester is notable, too, for his willingess to give safe harbor to Quakers, a religious sect that was persecuted elsewhere in New England with floggings and even having their ears cut off. As late as 1870 only about 100 families lived on the island, surviving by farming and fishing. Initially summer visitors tended to come from Greenport, where there was access from New York by rail and to the New England steamboat lines.
The Nature Conservancy's undeveloped Mashomack Preserve covers about a quarter of the island. The 2,039-acre tangle of tidal creeks, oak forests, fields, and marshes has more than 20 miles of trails for hiking and bird watching. A wheelchair-accessible trail begins near a visitor center and gift shop. In July and August, Mashomack is open to visitors seven days a week from 9 a.m. to 5 p.m.; off-season hours are more limited, so it is a good idea to check the Web site before heading over. There is a suggested donation of $2, $1 for children. Pets are not allowed.
Popular swimming spots are Crescent Beach and Wades Beach, where there is a shallow, roped-off area good for kids. In the height of summer at Crescent Beach, sights include seaplane and yacht arrivals of guests of the Sunset Beach hotel. Those looking to eat without breaking the bank can try the Pridwin Hotel and Restaurant, known for its Wednesday night cookouts and live music in season. Wades Beach is more of a family-oriented scene, with no nearby food choices, but a few picnic tables. Parking is by permit at all of the island's beaches; week, month, and season-long passes are available at Town Hall for nonresidents.
Public golf can be played at the town's course, Shelter Island Country Club, which has its own restaurant, in Shelter Island Heights. A miniature golf course (and ice cream parlor!) at the Whale's Tale, 3 Ram Island Road, is a good way to entertain the kids seven days a week in season.
Food choices that stay open year-round include Sweet Tomato's Italian restaurant, Stars Café, Commander Cody's Seafood, and the Islander, which is open for breakfast, lunch, and dinner. Fish dinners are also available at Clark's Fish House, a recent welcomed addition that is open on weekends in the off-season, and upscale dining draws them in at Vine Street Café, La Maison Blanche, and 18 Bay Restaurant.
In the warmer months, there are a number of boutiques, antiques stores, and art galleries to visit around the island. As temperatures increase, so do the variety and number of restaurants, such as SALT Waterfront Bar and Grill, which frequently offers live music. Sunset Beach, an Andre Balazas property on Crescent Beach, has a pricey Mediterranean menu. The Dory also has a few well-known acts that make an appearance, and a bar or lunch and dinner menu.
Classical music is also alive and well in the summer at the Perlman Music Center, whose students come from around the world and which has performances that are open to the public.
History treasures include Sylvester Manor Educational Farm, which opened recently to the public on 243 acres. Monthly tours of its historic manor house are a recent option added in winter, and in the summer, the farm offers organic vegetables and many programs for all ages but especially children. The farm also offers performances by traditional musicians and literature and nature-oriented activities at its annual Plant and Sing festival held each fall. The Havens House is a 1743 farmhouse now run as a museum by the Shelter Island Historical Society. A fun outing is taking a kayak or rowboat across Coecles Harbor to see the log cabin built a century ago by a borax magnate on Taylor's Island. It can also be accessed by foot at low tide from Mashomack Nature Preserve. It is run by a foundation dedicated to its restoration, which is ongoing.
In season, paddleboards, sailboats, mopeds, and kayak rentals are available, at Venture Out Sporting Goods, Piccozzi's Bike Shop, Coecles Marina, and Shelter Island Kayak Rentals. Those who rent bicycles should be aware that some of the hills can be quite a challenge for a novice, and the Island does not have bicycle lanes.
A 10K race each July draws thousands from around the world to compete. Also in July, the annual Chamber of Commerce fireworks celebration is popular with locals and visitors alike.
Options for getting to the island include the South Ferry, which departs from North Haven, or the North Ferry, departing from Greenport, with both welcoming cars and/or passengers.
Those with their own boats can anchor at various locations, such as Dering Harbor or Crescent Beach, and those preferring amenities can consider boatyards such as Coecles Harbor Marina, Dering Harbor Marina, or the Island Boatyard.