Shelter Island: check in at Long Island's secluded oasis of calm

When you’ve had your fix of New York’s bright lights, make for the quiet of Shelter Island, says Dan Rookwood
Dan Rookwood13 November 2015

New York is famously the city that doesn’t sleep. Not surprising given the cacophonous din of horns, sirens and pneumatic drills that serves as the incessant soundtrack of the insomniac. Whether visitor (like you) or resident (like me), at some point you’re going to want to get out of the Big Smoke and breathe some fresh air.

Where to go? At the end of a long week, hipsters tend to head upstate to the Catskill Mountains, but many New Yorkers head east to Long Island. Those who like to flash the cash tend to stick to the Hamptons. Further east, Montauk is very much a party town these days. Shelter Island is, as the name suggests, an oasis of calm. Lodged like a garden pea between Long Island’s two prongs — the South Fork and the North Fork — it is a quiet island inhabited by the prim and prosperous. Pretty dull to live there year round, I’d think, but lovely for a weekend escape.

The ferry from the scene-and-be-seen Hamptons of the South or the bucolic wine country of the North only takes a few minutes, but it transports you to a place of literal and metaphorical separation. The knots in your neck loosen as you chug across the water to the island, a 27 square mile oasis of hiking and biking trails, bay beaches and salt marshes.

No sooner had we rolled off the ferry and turned the corner than we happened upon our hotel, The Chequit, which sits commandingly atop the hill of Shelter Island Heights, with views down to the water. Built in 1872 by the local Methodist church as a dining hall for the community, the sprawling house was later converted into a 37-room hotel, which in its heyday hosted such luminaries as Marilyn Monroe, Frank Sinatra and the Kennedys before lapsing into dilapidation. It has recently been refurbished as a boutique hotel that sensitively retains the warmth and character of its storied history, while dispensing with the net-curtained chintz of a down-at-heel B&B.

The hotel’s restaurant Red Maple, named after the vast tree in the courtyard, has already become the hot place in town, specialising in sharing plates of locally sourced food such as Montauk fluke crudo, South Fork asparagus and Fishers Island oysters. The food rivals that of the flashier Sunset Beach nearby, the chic eaterie run by André Balazs of Chiltern Firehouse fame.

Our room was the size of our entire Brooklyn apartment and decorated in a palette of pale blue and white with tasteful nautical touches. It boasted a free-standing claw-foot bath as well as a rooftop terrace complete with hammock and swing seat — perfect for sinking into a good book. The bed was massive and though the walls are rather thin (not much the renovators could do about that without completely gutting the place), we slept the deep and restorative sleep of the absolutely bloody knackered.

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After an exploratory (ie, nosy) jog the following morning along a billionaire’s row of vast waterfront mansions, each with its own yacht dock — how the other half per cent live! — and a breakfast of fruit, homemade muesli and freshly baked pastries, which we ate on the verandah, we set off to pootle around the island, where the leaves were just beginning to turn various autumnal shades. Life here is slow and after-you-please polite. The speed limit is 35mph and there are no traffic lights. I stopped to get cash from an ATM and the guy in front of me shook my hand and exchanged pleasantries. This is two hours but a million miles from Manhattan.

Shelter Island is the destination, but the journey through the vineyards and farms of the North Fork is just as enjoyable. We hadn’t stopped en route, so we decided to hop back on the car ferry over to the fishing village of Greenport, which, from the looks of the delis and coffee shops and the beards and tattoos, is on the cusp of hipsterfication. It is also the gateway to some cracking wineries that have given the North Fork the somewhat hyperbolic moniker of the Napa of New York, and the highway is lined with farm stalls selling local honey, homemade fruit pies and, at this time of year, pumpkins of all shapes and sizes.

Within stumbling distance of Greenport’s centre is a majestically situated winery called Kontokosta with a tasting room on a bluff overlooking the sound. We bought a bottle of rosé and took it to a nearby pebbled beach where we watched a pair of rare ospreys swoop against cobalt skies. Collecting shells and bleached stones as we watched the maritime world bob by, we began to formulate the pipe dream of buying a weekend beach house out here. ‘Well, why don’t we?’ said Sam. And so, no word of a lie, we’re returning next weekend to start the house-hunt.

Check In

Virgin Atlantic flies five times daily from London Heathrow to New York. Fares start from £515 (0844 2092 770; virgin-atlantic.com). Rooms at The Chequit start from £127 per night (thechequit.com). For more information onNew York State, visit nylovesu.co.uk

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