Shelter Island Heights, New York

Photo: Jane Beiles via The Chequit

Wanted: A weekend outside of the city. You need to slow down, sleep in, and ignore your phone. Some sunshine, fresh air, and blooming flowers would be nice. So would a view of the water.

Shelter Island is the perfect escape from New York City. The 8,000-acre island sits at the eastern end of Long Island in between the North and South Forks. It’s surrounded by the Shelter Island Sound on three sides; Gardiners Bay is on the other. Nearly one-third of the land—made up of woodlands, freshwater marshes, tidal creeks, and beaches—is protected. Victorian buildings dominate the architecture. Plus it’s still quiet right now. Summer residents, some of whom have been visiting the island for generations, have yet to arrive for the warmer months.

Nathaniel Sylvester bought Shelter Island from the Manhansets in 1651. The merchant built a provisioning plantation to ship sugar and molasses, rum and tobacco back to his native England. A real community didn’t develop until after his death in 1680. Religious camps and summer cottages eventually followed. Its popularity truly grew after World War II.

Photo: The Chequit

One of those former religious retreats is now a charming inn. The white building with green trim was built in 1872. It recently underwent major renovations and opened as the Chequit three years ago. The inn’s thin walls, hardwood floors, and fireplaces were left intact. So was the wide porch, which boasts a view of the Peconic River.

Thirty-seven whitewashed rooms are now sparsely decorated. You’ll find a king-size bed with 400-thread-count sheets and a plush duvet in your superior king room. There’s a little sitting area with a bright yellow chair and a succulent on the wobbly table. Turkish throw rugs, brass lighting fixtures, and a wide-brimmed straw hat complete the decor. C.O. Bigelow Apothecaries bath products and Further hand soap are in the bathroom near the rainfall shower. But the best part might be what’s missing. There isn’t a television in the room.

You arrive at the Chequit after a quick—just eight-minute—ferry ride from Greenport. The inn, like almost everything else on the island, is just a short walk from the dock. Since there’s no official check-in time, you don’t have to wait to settle into your room. You’re given a rundown of breakfast and evening drinks before you go upstairs. A hearty buffet is served each morning. You can eat by the fireplace in the lobby or outside on the porch. The menu changes daily, but yogurt parfait, homemade granola and jam, and seasonal fruit are always included. Bloody Marys and Mimosas are offered, as well. Or a lighter breakfast can be delivered to your room.

Then beer and wine, both on tap, are served during an extended happy hour in the afternoon. It’s the ideal way to relax after swimming, kayaking, or hiking all day. The Chequit has totally decompressed you already.


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