On the East End, there’s the North Fork and there’s the South Fork, and then there’s a little something in between. Shelter Island was cool before becoming a hashtag on Instagram, you just didn’t know it unless you, well, knew it. Settled in the mid-1650s, around the same time as the towns lining the twin forks, this small town spans less than 30 square miles, and proudly belongs to neither the North Fork or the Hamptons. Shelter Island is its own entity, but at least has two ferries to get you on and off the island, should you ever so choose.
Shelter Island was once inhabited by a peaceful tribe of Native Americans, the Manhanset tribe, that called their home Manhansack-aha-quash-awamock, which translates to “an island sheltered by islands.” Quickly inhabited by settlers, much of the island’s history is still present in the modern day, serving as a draw for people to now find their own home on Shelter Island, or just simply come and play.
The journey through Shelter Island is longer than you may expect with all of the stops you can, and should, make. Enter through the North Ferry from Greenport, the South Ferry from North Haven, or by boat, and you have access to some of the island’s most popular eateries. A historic and grand hotel, Chequit Inn, has undergone a needed facelift in the past few years, and now serves as one of the notable places to both stay and eat. Locals and visitors alike find French-inspired cuisine at Marie Eiffel Market overlooking Dering Harbor, while The Dory offers the true-local experience as a casual, classic American pub.
With words like “local” and “organic” populating nearly every menu, farming and fisheries themselves play an essential role to the Shelter Island way of life. What began as a Native American hunting ground later becoming a historical and educational establishment throughout the course of history, is now known at Sylvester Manor Educational Farm. With a mission of cultivating, preserving, and sharing the land, buildings, and stories of the historical property, they encourage thought about the importance of food, culture, and place in our daily lives.
“At Sylvester Manor Educational Farm, there is always something going on,” says the organization’s director of programs and community outreach, Kim Folks. “The key for us is to offer diverse programming year-round, and make it as accessible as possible.” With events including concerts with award-winning musicians on and off premises, Shakespeare themed weekends, and more, there is much to enjoy.
“Our house concerts and historic house tours open the Manor doors to the public to enjoy the most intact plantation home north of Virginia,” Ms. Folks continues. “We encourage visitors to come with their lawn chair, family, friends and picnic baskets for any of our outdoor creek side concerts as well.”
Preservation of the island isn’t just of importance to the locals, but to the health of the environment on and around Shelter Island. Mashomack Preserve encompasses nearly 2,100 acres and is home to hundreds of species of plants and wildlife. Marked trails are available to hikers only, and visitors are encouraged to only take out what they take in. The Nature Conservancy, which partners with many other environmental organizations, aims to keep the area beautiful and preserved while promoting the enjoyment and conservation of nature to all.
A narrow road bordered by water on either side offers a beautiful drive to a secluded little spot that has a lot of – you guessed it – history. The Ram’s Head Inn, just off of Ram Island Drive, was built in 1929 as an inn, and is still used as one today. The original structure echoes with times past as a registered historic physics site. That’s right, in the mid-1940s several physicists held themselves up in the inn as they tackled some of the most important and complex problems of quantum physics, and succeeded in a fundamental understanding of what was previously a mystery to many.
On the food side, The Ram’s Head Inn restaurant serves New American food that focuses on seasonal farm-to-table food, with lots of seafood of course. With executive chef Matt Murphy now at the helm, the season is sure to be a delicious one. “His passion for food and knowledge of the abundance of ‘local delicacies’ make him the perfect fit for the Ram’s Head,” shares owner Linda Eklund. Expect dishes like poached halibut, Long Island Crescent Farms duck confit, and rack of lamb, all accompanied by greens and herbs from the on-premises garden.
Should your journey through Shelter Island take you on an alternate route, you will find more inviting restaurants and things to do. Venturing toward Shelter Island Sound you will come upon one hotspot that is very Hamptons-esque; Sunset Beach. Yellow and white awnings and beach umbrellas are the waterfront establishment’s signature, letting boaters know they’ve reached the right place before they even hit the shore.
Messy and undone, yet sophisticated and oozing with summer cool, the bikini-clad and happily tan are mingling in the restaurant and the sand just a few steps across the way. Owned by the famed hotelier André Balasz (think the infamous Chateau Marmont in Los Angeles), the boutique hotel, restaurant and bar offers coastal Italian fare and cuisine reminiscent of the French Riviera. And don’t forget that signature pink summer drink you just can’t say no to; the self-described “house elixir;” a chill glass of rosé. À votre santé!
Traveling further down Shore Road, you will find the Pearlman Music Program and the Pridwin Hotel. Other notable establishments on Shelter Island include Vine Street Café, SALT restaurant, Shelter Island Country Club, Gardiner’s Bay Country Club, and seemingly endless beaches with access to numerous bays, harbors, and estuaries.
To know the beauty of Shelter Island, you must experience it for yourself. Take the time to explore the ins and outs, sip and dine, and stay and play. Teeming with history and culture, Shelter Island is a gem of a place that no one should pass by.