As some NYC residents vacate the boroughs for summertime escapes, Shelter Island provides a setting of resplendent beauty, quiet isolation and thoughtful adventure. The island’s motto “life between the ferries” nods to the fact that it’s only accessible by car-carrying boats—one of which comes from Shelter’s southern neighbor, Sag Harbor and the other, from the North Fork’s Greenport. Shelter Island’s separation from its social southern sibling, the Hamptons, is more than just physical—it’s spiritual. That isn’t to say one can’t sip signature cocktails and dance into the night or gaze at yachts from a boat-shaped bar in a marina. It means that, with the extra effort of crossing a slender body of water, fewer people filter into this hideaway. And one of the best experiences you can possibly have while there is a quiet stroll by the water.
An epicenter of island activity, Sunset Beach pairs 20 guest rooms with a bustling bar, sandy-floored outdoor restaurant and summertime boutique. It’s the vision of acclaimed hotelier André Balazs and it rises around one exquisite tree and opposite the public Crescent Beach. You don’t need to stay here to enjoy much of its splendor, but make reservations for brunch or dinner if you aren’t.
Marie Eiffel Market
Whether you’re searching for epicurean delights or simply in need of a sandwich, Marie Eiffel Market will satiate. The French proprietor of this restaurant/specialty store hybrid can often be seen behind the counter, serving locals or visitors. It’s a hotspot for breakfast, where it’s easy to order and take up a spot at one of the tables out back—which come with a marina view.
Black Cat Books
To equip oneself for the peace and quiet of the island, a visit to Black Cat Books yields many treasures. The store stocks over 20,000 fine and used books—including rarities and first editions. Snag a beach read or finally commit to a vintage collectible. Black Cat’s owner Dawn Hedberg also buys, if you’re looking to offload a previously devoured paperback.
Ram’s Head Inn
Situated in a remote section of this already remote island, the historic Ram’s Head Inn offers serenity mere steps from the beach. From 17 quaint rooms to the destination-worthy brunch menu, the hotel draws guests seeking solace and sunsets. With a view of Coecles Harbor and a sloping lawn strewn with Adirondack chairs, the outdoor restaurant taps into seasonality—and fresh fish dishes are always reliable.
Mashomack Preserve covers one-third of Shelter Island. Some 11 miles of coastline, forests spliced with tidal creeks, and lush marshland comprise the 2,039-acre preserve. Well-marked trails range from simple strolls to miles-long hikes. Flora and fauna take hold of all senses and special wildlife sightings are not uncommon.
You’ll find no place more authentic on Shelter Island than Commander Cody’s, the no-fuss fried-fish-and-barbecue restaurant of Jim Hayward. Located inside and around the addition of a house Hayward built for himself in the ’80s, the restaurant’s saltwater fare is caught daily. The barbecue portion of the menu draws inspiration from Hayward’s Charleston childhood. Regardless of the direction one takes, you can’t go wrong. You can also order in advance and pick-up, but it’s certainly fun to dine on-site and BYOB.
The Perlman Music Program
An important part of The Perlman Music Program may be intensive summer training programs for emerging string talent, but for everyone else, their summer program at the Clark Arts Center sees exquisite classical music performances within reach. Founder Toby Perlman dreamed of providing musical education to those in need of further nurturing (regardless of their financial status) and, thanks to this vision, the island benefits through its side product of dulcet tones.
Hero image by David Graver