Travel Back 50 Years in Three Hours at Shelter Island

By Richard Levy

Taking the 10-minute ferry to Shelter Island from Greenport or Sag Harbor is like boarding a time machine.

When you drive off the ferry, you’ve arrived in a magical, storybook island covered with gingerbread houses, windswept picturesque beaches, colorful harbors, 100-year-old trees, wildflowers, captivating vegetation, deer, pheasant and magnificent osprey on their huge nests on top of telephone poles keeping their eggs warm until they hatch.

This 8,000-acre island nestled between the North and South Forks of eastern Long Island, is one-of-a-kind island Darwin would have applauded. The place to stay, if you’re lucky enough to score a reservation, is the luxurious, old world Ram’s Head Inn. First opened in 1929, this magnificent hotel has been attracting a well-heeled, sophisticated crowd who have appreciated its privacy and unbridled elegance.

There’s only 22 rooms and they book up quickly by knowledgeable travelers.

The hotel’s new owner, the elegant and visionary Andrea Carter, has taken this gem and added spectacular new touches. Its restaurant is one of the best on the island. The gorgeous veggies from Carter’s organic garden are part of her farm-to-table sustainable food sourcing that go into her chef’s mouthwatering dishes.

She’s added a fabulous oyster tasting every Thursday at 5 p.m. where a diner can devour three different varieties of local oysters, and an “oyster shot,” where an oyster and its liquid is dropped into a shot glass and covered with a splash of Bloody Mary. It’s a decadent experience.

For dinner, start with their outrageous confit of duck spring rolls, then try to-die-for entrees including pan-roasted striped bass on sautéed spinach, seared scallops or herb crusted halibut and delicious mini crab cakes.

Ram’s Head Inn has its own lovely private beach, tennis court and you can even play on a full-size bocce court.

If recreation is your thing, there’s a world class golf course that easy to get on and miniature golf for the kids. There’s the Mashomack Preserve, more than 2,300 acres protected by The Nature Conservancy, for cycling or hiking. It’s perfect for bird watching and to view magnificent ospreys, herons and egrets.

Explore the twisting winding roads and discover little coves embracing the sea, decorative houses and mansions.

At Crescent Beach, stop for a drink at the Sunset Beach Hotel with its “Sex and the City” crowd. There are some lovely restaurants on Shelter Island, but none come close to the outstanding food you’ll find at the Ram’s Head Inn.

The island also has quaint shops filled with all sorts of merchandise.

Marie Eiffel Market in town is like a food market in Paris. They’ll make you gourmet sandwiches to devour on their deck in back of their shop with astounding views of the harbor.

For the best home-made corned beef hash and eggs ever, visit Crazy Beans in Greenport.

On the way home on the North Fork, stop off at a Long Island winery for a free wine tasting. Don’t wait. The post-COVID-19 explosion of folks desperate for a getaway is real, and every place is booking up quickly, including the Ram’s Head Inn.

Get out before it’s all booked up through Labor Day weekend, or better yet, book a week or long weekend in September or October. That’s my very favorite time to be on magical Shelter Island.

When you depart this endearing island, you’ll be relaxed and relieved of your stress.

Hastings-on-Hudson resident Richard Levy is a former advertising “Mad Man” creative director and now a travel writer. He’s also an inventor of innovative new products and is writing and illustrating a new children’s book. You can contact him at RichardLevyTravelWriter@gmail.com.

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