Jessica’s Picks: Shelter Island

August 22, 2014

It’s no secret that New Yorkers flee the city like rats on a sinking ship every weekend between May and September. Presumably to give the actual rats some breathing space. Whether they’re extending an invite or angling for one, most New Yorkers know that the most secluded beaches, the clearest ocean water, the most picturesque coastline, and the freshest oysters are just 2-3 (alright 8, but only on Labor Day weekend) hours from the city. They also know that a few days of respite between Southampton and Montauk is the only antidote to a sweaty New York work-week. And you don’t even need to pack a passport.

Shelter Island, nestled between the bucolic North Fork and the beachy South Fork, was historically referred to as the Unhampton. Enterprising real estate agents have started passing it off as the “New Hampton,” though it is anything but. Comfortingly antediluvian, Shelter Island has nothing to prove and nothing new to offer, which of course makes up its enormous charm. Quaint, communal and peaceful, it is a place where time has stood comfortingly still.

Part of the joy (and hassle) of Shelter Island is that you can only reach it by ferry, either from Greenport in the North or Sag Harbor in the South. The extra 10 minutes one needs to cross the bay is just enough to acclimate to the slower pace of the island, and in some cases, keep those out who don’t know how to slow down at all. In addition nearly half of the island is owned by the Nature Conservancy – The Mashomack Preserve – which means the island will always be somewhat sparsely populated and heavily forested, which lends it an occasionally primeval feeling. There are secret hikes and beaches and sandbars, even little satellite islands like Ram and Little Ram Island or Taylor’s Island, with one beautiful early 20th Century lodge (and one tombstone) on it. The beaches are covered in the most spectacular shells and the occasional jellyfish. The bay water’s slightly warmer temperature is conducive to the strangely beautiful creatures, and should you get stung (as I did this summer) the pain is short and tolerable, though shocking.

But don’t panic. There is cell reception and high speed internet on the island as well as a few wonderful restaurants and one of my favourite antique stores in the country!

Where to Eat:

The best breakfast cappuccinos are without a doubt made by Handsome Ned (everyone’s favourite waiter) at Sunset Beach, Andre Balazs’s old standby. Later in the day, the place becomes packed and the mood changes (this may be the only party scene on the island, and gives those looking for one a run for their money), but mornings are idyllic. Cross the street and head directly for the water to sleep off your breakfast food coma in the sand.

Check out Schmidt’s Market for deliciously old-fashioned sandwiches and local produce, as well as good fresh fish.

Reddings is a one stop general shop for all your weekend newspapers and French inspired picnic sundries, including delicious salads.

Tuck Shop is a must for ice cream sundaes the size of your face, with flavors you haven’t seen since 1987 (Superman, anyone?). (75 Menantic Road)

Best become a member of the Gardiner’s Bay Country Club because after a round of eighteen holes, there is nothing better than sitting down for lobster in the dining room and feeling like you’re the youngest person on the planet. Remember: no denim, so bring your best wrap dress to change into!

If you are hoping for a slightly more urbane meal, Vine Street Cafe can compete with your favourite New York city restaurant  with a strong emphasis on locally sourced produce and seafood.

What to do:

Rent a bike at  JW Piccozzi and explore the island. Route 114 connects the northern part of the island with the southern and is very easy to navigate.

My favorite neighborhood, Shelter Island Heights (close to Sunset Beach), is one of the most pristinely preserved neighborhoods in New York. Designed by Frederik Law Olmsted (who went on to design Central Park) and Robert Morris Copeland (who designed Oak Bluffs in Martha’s Vineyard), many of the houses are built in the ornate and romantic style of the late 19th Century.

Close by is Sylvester Manor, an extraordinary 243 acre estate that dates back to 1652, which has been converted into an educational farm and can be visited most weekends.

Make sure to check out the farmer’s market which sells some of the best local cheeses, breads, pies and produce near and far.

Finally, if you’re stuck with no plans on a Friday, head down to the Perlman Music School named after the legendary violinist Izhak Perlman, where children with profound and special musical gifts are invited to participate an intensive residency during the summer and perform free concerts every Friday.

Don’t leave the island without leaving at least half your paycheck at Marika’s Antiques, my favourite antique shop in Suffolk county. With its enormous selection of midcentury modern furniture and objects, but also the odd BIedermeier console, you will have a whole day cut out for you, if you happen to be neither interested in nature, music or food.




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