Travel | August 26, 2022 7:38 am

Why You Should Visit Shelter Island the Next Chance You Get

A special and semi-secretive escape from the city has gone through changes, but its small-town charm remains

The view from The Pridwin, a summer and sometimes off-season staple of island life
The view from The Pridwin, a summer and sometimes off-season staple of island life
Cape Resorts

Things don’t change very quickly on water-locked Shelter Island. Lately, however, a spate of old, beloved eateries with new ownership and a new lease (literally) on life are making the ferry lines a bit longer than usual. 

This isn’t the observation of an outsider or island dabbler. I’m from there. Like, from-from there. Not a “harelegger” (the mysterious term coined for those born, quite literally, on the island), but since the age of two when my parents moved my three older sisters and me from the Long Island side of the Queens border. I graduated from the square red-brick K-12 school on Route 114 with 15 kids in my class, most of whom I’d known all my life, and subsequently high-tailed it out of there, lured by the siren song of New York City and the influence of too many issues of Interview magazine. 

But after all these years, the place I dream of being all the time is back on my former island home. I get it now; it’s special. It’s the kind of place that gets under your skin with its soft, undulating roads decorated in dappled sunlight; swathes of unspoiled, unbuilt-upon wilderness; rocky, quiet beaches; tiny-town feel; and that ultimately unique bit: It’s literally separated from the mainland. The only way on or off is a ferry boat (which, for a six-year spell after we first arrived, my dad worked on as both a purser and a captain, back in the days when there was only a rusty chain separating the first car on from the water in front of it).

The reputation of Eastern Long Island as a can’t-miss summer weekend escape destination deserves the soaring popularity it receives, both historically in the Hamptons and more recently on the vineyard-laden North Fork. But that attractiveness has also revved the engine of change—some good, some not so good. But plunked in the middle of the forks, Shelter Island has its own particular slow-lane vibe. When things change here, they don’t so much alter as morph. Even hot spots like hotelier Andre Balazs’s ever-popular, see-and-be-seen Sunset Beach isn’t so very far from its origins as a beachy snack bar-turned-summery restaurant and motel built by the Kraus family. And Vine Street? That building began as a welcoming, homey bakery owned by a sweet old German couple, the Schmidts—some of that vibe still permeates the gracious hospitality of owners Lisa and Terry Harwood. 

Several old, beloved haunts have received excellent make-overs recently, and while the paint is fresh on many of them and their servers are still getting their sea legs, I can say from my own formerly uber-local POV: They’ve got promise. A bit of nostalgia mixed with a fresh eye for detail is a good recipe for success here, and as the dog days wind down in summer 2022, be sure you check out one of these six worthy spots before the last boat leaves the slip. 

The Pridwin Hotel & Cottages
The Pridwin Hotel & Cottages
Cape Resorts

The Pridwin Hotel & Cottages

After shuttering for an ambitious two-year renovation, the glorious, seven-acre, water-view Pridwin Hotel has reopened its 33 rooms and 16 cottages. Even better, they re-launched a newly designed restaurant and bar, the Terrace and the Crescent Bar, respectively, and right in time to celebrate the Pridwin’s 95th anniversary. Owned since 1961 by a local family, the Pridwin has long been a summer and sometimes off-season staple of island life. (My husband and I got married here.) There’s good reason for the Pridwin’s staying power: From the often fresh-caught fish on the menu from the third-generation owner, Greg Petry, to the heart-stopping sunset views from the second-floor porch, it’s been one of the island’s best-kept secrets for an awfully long time. The luxe changes here are delightfully mindful of the hotel’s past, with rooms and nooks named for the Petry family, yet bring it into the present with thoughtful details from designer Colleen Bashaw, who combined classic color with playful upholstery and other eye-catching design elements. Grab an excellent Hemingway Daiquiri from the updated cocktail list, pull up an Adirondack chair on the porch and get a breathtaking front-row seat for summer’s breezy coda. 

The Eccentric Bagel
The Eccentric Bagel
The Eccentric Bagel

The Eccentric Bagel

Far as I can remember, Shelter Island has never, ever had a dedicated, homemade bagel shop, and since Darryn and Amy Weinstein opened the door of this cheerful little dough factory, it’s been packed daily. Humming along to the sounds of hot, fresh bagels being poured into the stainless steel bins at the front counter and ‘80s music videos on constant play from the high corner TV, the Weinsteins offer around 19 different types of bagels, excellent cream cheese options, breakfast and lunch sandwiches with local-winking names like the Hay Beach and the Dering Harbor, and solid coffee. In 1976, this spot opened as a tidy little grocery, deli, and butcher shop built and owned by one Mike Zavatto (my dad); I spent a lot of time making sandwiches here. If I can walk in that building and feel happy about what’s going on, trust me — it’s good stuff. 

The Ram’s Head Inn
The Ram’s Head Inn
The Ram’s Head Inn

The Ram’s Head Inn

It’s not easy to start a new business in the middle of a pandemic, save one in an area in which you have no experience. Seeing how newly minted owner Andrea Carter has embraced both her new industry and the 90-plus-year-old charm of this stunning, wood-shingle-clad spot with its sweeping lawn and view of Coecle’s Harbor, you might say she’s embodying the spirit of its original owner (Joan Covey), who took a chance on building an inn on a remote island during the Great Depression and succeeded. Carter gave the charming 17-room inn and restaurant a beachy refresh, and added weekly events like oyster night and fireside author readings in a partnership with a local book shop, Finley’s Fiction, along with special event dinners, live music and wellness classes. In addition to maintaining the comfy-chic vibe, she also held onto the Inn’s longtime excellent chef, Joe Smith, who found his penchant for seasonal dishes—more often than not sourced from the local waters, farmers and the Ram’s Head’s own on-site garden—under former renowned Ram’s Head Inn chef and CIA prof, John Barton. It’s a bit out of the way, but the drive on Ram Island’s rocky, osprey-dotted peninsula is gorgeous, and an evening spent here dining al fresco on the pillared back porch is worth the trek.

18 Bay
18 Bay
Francesca Frasco

18 Bay

When this divine restaurant, owned by chefs Elizabeth Ronzetti and Adam Kopels, first moved from Bayville, Long Island, to Shelter Island back in 2013, I remember thinking: This is amazing, but they’ll never get people to adhere to such strict menu parameters. You can’t tell someone paying $125 a pop that this is the only menu…or can you? To wit: 18 Bay serves, then, now, and hopefully evermore, a weekly-changing four courses—the first, a set quatrain of uber-seasonal starters, followed by a fresh daily pasta course, a choice of one of two proteins for your main and a set dessert. Save for an allergy or aversion to eating meat, there were no changes or substitutions. Every meal and every dish is 100% inspired by whatever wonderful fresh things Kopels and Ronzetti are able to hyper-locally source. It’s become such a favorite, Kopels and Ronzetti had to move to a bigger space this year. New this year (in addition to the digs): A 4-course pasta tasting menu on Sundays and takeaway boxes to upgrade your beach or poolside eating options

Kyle's
Kyle’s
Shelley Clark

Kyle’s

I may get some guff (islanders like nothing better than giving you guff) for including this sweet little former post-office-turned-bakery-turned-take-out-window-turned-back-into-a-restaurant. Indeed, it’s not new, but it certainly has morphed. Owner Kyle, who goes by one name only (Kyle is actually her last name) has an uncanny ability to roll with change and yet still remain deliciously relevant. If all she did was make her entirely unforgettable jelly donuts—a slightly crispy, golden exterior rolled in sugar, its pillowy insides the perfect resting spot for a nestle of raspberry jelly—she’d probably do just fine. “The donuts have been published in a novel by an author here who used to bring them to his mistress,” Kyle told me recently. (Pro tip: They’re so popular, they have to be pre-ordered). She closed her doors during the pandemic, offering baked goods and take-out meals and special orders. During that time, she took the opportunity to renovate the back deck into a tranquil, lovely sitting area from which to nibble on her excellent Linzer tarts, almond croissants and coconut macaroons. In addition to the bakery in the back, she’s re-launched as a breakfast- and lunch-only eatery, where you can hang out in the newly spiffed up, unfussy dining room or breezy front porch and linger over succulent lobster eggs Benedict or souffle-like frittata of the day, served with crispy, onion-y, thinly sliced potatoes, and potent, spicy Bloody Marys.

The Chequit
The Chequit
Zack DeZon

The Chequit

First, it’s pronounced chee-quit (not check-it). Built in 1872, this island icon is a stone’s throw from the North Ferry and easily walkable from the Greenport side. Recently purchased by the Soloviev Group, The Chequit now holds three eating and drinking denizens run by chef Noah Schwartz (of Noah’s in Greenport): Weakfish Sushi & Noodles; Heights Café & Wine Bar, a day-to-night breakfast and vino spot; and the Tavern, probably the most anticipated opening of all three. The Tavern was closed to non-hotel guests for several years under the last set of owners. Soloviev appears to have a deep appreciation for both community and nostalgia, and took great pains (and expense) to restore the long-gone center bar, add back the much-missed pool table, and spiff up the rest with gorgeous leather booth seating, deep teal-green walls, and lots of clubby nooks in which to sit, sip a cold beer and catch up with old or new friends over kicked-up versions of pub fare. 

Leon 1909
Léon 1909
Douglas Young

Léon 1909

There’s been so much local gossip (most of it wrong) about this place since word got out that the old Capital One Bank branch was slotted to become a restaurant. Owners Valerie and Robert Mnuchin have certainly plugged a lot of resources and effort into every detail, ripping the building down to the studs and starting over. Named for Valerie’s grandfather, Léon’s soft opening in early August revealed an airy, newly lofted ceiling and a central wood-fired oven where crispy-skinned roast chicken, seared rib-eye steaks, and tender roasted pork shoulder get the live-fire, Provencal-skewed treatment.