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Shelter Island: Things to do, eat and see in the 'un-Hamptons'

Not much changes on Shelter Island. In fact, the only stir over the past year was the opening of one hotel, one coffee shop, one restaurant and one boutique — all of which are under one roof, The Chequit’s.

Known as the “un-Hamptons,” Shelter Island boasts zero traffic lights, just two liquor stores and under 3,000 residents. Unlike nearby East End destinations like Montauk, the island is unapologetically and consciously in a state of repose.

On Shelter Island, plan to relax. Here’s how.

Where to go

Shelter Island is nestled between the South and
Photo Credit: John Paraskevas

Shelter Island is nestled between the South and North Forks of Long Island. Crescent Beach, one of a handful of tranquil beaches there, is as Hamptons-esque as it gets, thanks to the glitzy Sunset Beach hotel nearby.

The bulk of Shelter Island's 27 square miles are peacefully residential. Shaded streets are fit for neighborhood strolls, but consider renting a bike from Piccozzi's Bike Shop ($25 per day; 177 N. Ferry Road, 631-749-0045, Opt for a full-day rental and cycle east to Ram Island to spot historic manors perched on the pristine coast. Most beaches here are secluded and perfect for a private dip.

Among the main reasons for Shelter Island's lasting tranquillity, is Mashomack Preserve, which encompasses nearly a third of the island and was made into a nature sanctuary more than 20 years ago to curb development. Only hiking is allowed (even jogging is forbidden) along the preserve's marked trails. Walk past white coastlines, oak woodlands, freshwater marshes and tidal creeks, and keep a watchful eye out for the endangered ospreys populating the preserve.

Where to eat

For coffee and breakfast, visit the dockside Marie
Photo Credit: The Chequit

For coffee and breakfast, visit the dockside Marie Eiffel Market (184 N. Ferry Road, 631-749-0003, in Shelter Island Heights. Helmed by a Parisian pastry chef, just-baked croissants and pain au chocolat are best enjoyed in one of the shop's Adirondack chairs overlooking a sleepy harbor.

At Commander Cody's Seafood (41 Smith St., 631-749-1815), the owner, a veteran fisherman, serves local seafood and lobster rolls at a restaurant attached to his home. The island's newest opening, Red Maple, pictured, (23 Grand Ave., 631-749-0183,, at The Chequit hotel, is casual but refined; find jalapeno-flavored calamari, skirt steak with chimichurri and trifles for dessert.

For dinner at Sunset Beach Restaurant (35 Shore Road, 631-749-2001,, ask for a table on the upper-deck (the restaurant, like a treehouse, surrounds a massive oak tree) and snack on creamy kale salad and red snapper. Then, head to the ground level for a beachy cocktail post-meal.

Where to stay

Known for its longstanding B&B culture, it's worth
Photo Credit: The Chequit

Known for its longstanding B&B culture, it's worth browsing the island's many Airbnb listings ( From Victorian summer cottages to contemporary loft-like shelters, aim for listings in Shelter Island Heights within walking distance of Marie Eiffel's croissants.

The newest property, The Chequit, pictured, (23 Grand Ave., 631-749-0018,, is a short walk from the North Ferry port. The new owners overhauled a dated inn, keeping its name while updating the décor from shabby to chic. Contemporary amenities, like tribal-inspired rugs, Turkish towels and oversized tubs, are among the subtle luxuries. Grab some coffee or a picnic to go at the hotel's White Hill Cafe.

How to get to Shelter Island

Shelter Island is only accessible via ferry. Ferry
Photo Credit: Doug Kuntz

Shelter Island is only accessible via ferry. Ferry service is available on both the North Fork from Greenport and the South Fork near Sag Harbor, on a first-come, first-serve basis; if you're driving from the city there tends to be less traffic on the way to Greenport. By train from NYC, take the Long Island Rail Road to Greenport, just steps from the ferry.

North Ferry: $11/one way vehicle and driver ($2 each additional passenger), $2/one way foot passenger (cash or check only); departures every 10 to 20 minutes

South Ferry: $14/one way vehicle and driver, $1/one way foot passenger (cash only); departures every 10 to 15 minutes


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