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Two and a half hours east of New York City and north of the Hamptons lies the North Fork, a 30-mile-long peninsula stretching from the town of Riverhead to Orient Point. Despite its proximity to Manhattan and its ritzy southern counterpart, the area feels like a world apart with its country roads dotted with stellar vineyards and farms. Day trippers head out here to sip wine, visit organic markets, or spend the day at one of many U-pick farms for berries, apples, pumpkins, and even Christmas trees, depending on the season.
Neighboring Shelter Island—reachable via a 10-minute ferry ride from Greenport Village—is equally charming, known for its peaceful beaches and bikeable roads. The 29-square-mile island with quaint homes, as well as impressive houses hidden behind tall, well-manicured hedges, feels like time stood still at just the right moment.
Once well-kept secrets of those in the know, the North Fork and Shelter Island are now unveiling new vineyards, restaurants, and hotels that are attracting an influx of visitors this summer and beyond.
Newest vineyards and wineries
The past two years saw exciting additions to the North Fork’s already prolific wine trail and its producers of award-winning reds, whites, and rosés. Meadowlark North Fork opened last summer in Cutchogue as the new sister property to Macari Vineyards in Mattituck. The 20-acre vineyard was created as an oasis where wine lovers can sip small-production and limited-edition vintages while wandering through lush pollinator gardens, thoughtfully designed to support the various species of butterflies and birds in the area, or lounging in one of the two modern farmhouse-inspired tasting rooms. The winery’s focus is on producing unique wines using biodynamic and organic farming methods.
Also in Cutchogue, Peconic Bay Vineyards reopened in May 2021 after an eight-year closure under new ownership with a cottage-esque tasting room and outdoor patio with fire pits overlooking its 148 acres of vines. One of the oldest (and largest) operating vineyards on the North Fork, the property offers tours, oyster happy hours on Fridays (when in season), and private picnics among the vines. Overnight stays in their red farmhouse, built in 1892, with private tastings and brunch are available. And a new tasting room with a state-of-the-art winemaking facility, hotel, spa, and additional acres of vineyard are in the works.
Over in Laurel, EV&EM Vineyards opened last spring with a sleek tasting room played up by a welcoming fireplace, a lounge-like tasting deck, an additional second-floor tasting deck overlooking the 40-acre property, and a cellar tasting room. The vineyard, now owned by news journalist and avid wine collector Dan Abrams, underwent a complete renovation that incorporates its dedication to sustainability, from the reclaimed wood used in the decor to the herbicide-free, biodiverse methods used in the grape-growing process. The inviting atmosphere, along with tours, a wine club, and private tastings, offers an elevated experience for both the novice and the enthusiast to talk about wine—and learn about winemaking.
Restaurant newcomers
Local, seasonal ingredients are the focus of the cuisine on the North Fork and Shelter Island, and that focus extends far beyond just farm-to-table restaurants. Here, it’s all about supporting the community that the food and beverages are sourced from—farmers, fishermen, purveyors, winemakers, and brewers—and connecting diners to the area. Opened late last summer, Léon 1909 brings a bit of Provence to Shelter Island. When it came to designing the eatery’s menu and décor, owners Valerie Mnuchin and her father Robert were inspired by Mnuchin’s grandfather, whom the restaurant is named after, and his travels to Nice as a child with his family. The Provençal-style fare by chef Mason Lindahl combines the best seasonal and local ingredients with French and Italian countryside dishes like whole roasted fish, charred cuts of grass-fed beef, and grilled artisanal flatbread. The proprietors aimed to create a place for people to gather for great food in an unfussy setting, and it’s safe to say they hit the mark with a welcoming dining room framed by a high trestle ceiling, warm lighting, and an open, wood-burning hearth that transports you to the Mediterranean.
At the newly transformed North Fork Table & Inn, located in Southold, Michelin-starred chef and restauranteur John Fraser and his chef de cuisine, Ryan Carroll, have created a menu that highlights the best seasonal ingredients the area (as well as Montauk, Block Island, and Rhode Island) has to offer. And as you can expect from almost any restaurant in Long Island Wine Country, the curated wine list is top-notch. The accompanying North Fork Food Truck out back serves up lobster rolls, burgers, and creative soft-serve ice cream desserts in a casual setting with communal picnic tables and outdoor games. Upstairs from the dining room are four boutique guest rooms, where you can extend your visit with wine and cocktail classes or tours of the local farms and vineyards.
Also fresh on the restaurant scene is Southold Social with its kitchen helmed by James Beard Award-winning chef François Payard. Highlights on the Mediterranean bistro-inspired menu, which changes based on the season and local farm offerings, include crudo, pasta dishes, and locally caught fish; and his special touch for desserts and presentation, which he’s known for, is as magical as ever. Grab a quick bite between vineyard visits or stock up on provisions for your weekend away at Southold General, a café, market, and foodie favorite also overseen by Payard.
Finally, for an out-east beach setting with a Greek island feel, reserve a table at Duryea’s Orient Point, the sister property to the popular Duryea’s Montauk that opened in the summer of 2020. Open from mid-May to mid-September, the waterfront restaurant boasts its own marina for guests who want to arrive by boat, indoor-outdoor seating, and a Mediterranean-inspired menu bursting with fresh seafood. On the weekends, their boho-chic Beach Club serves asado brochettes, lobster sliders, and a raw-bar menu that you can enjoy from umbrellaed seating by the water’s edge or tented lounge areas on the sand while a DJ plays ambient world beats.
Where to stay right now
The new hotels popping up in the North Fork rival those in the Hamptons, but they celebrate the area’s laidback charm and sense of community. Just unveiled this July in Greenport, Silver Sands Motel & Beach Bungalows is a hidden gem along Pipes Cove that feels a bit Wes Anderson-meets-the Long Island coast. Recently bought and fully restored by chef Ryan Hardy of Charlie Bird and Bar Pasquale in New York City and his business partner Alexander Perros, the motel is reminiscent of a bygone area. While the renovation was a complete overhaul, the owners stayed true to the property’s original mid-century décor with 1950s-inspired furnishing and cheery patterns throughout the 20 motel rooms and 14 cottages. The resort lies on 45 acres encompassing their private sandy beach facing Shelter Island, perfectly landscaped grounds, a salt marsh, and bird sanctuary. And because food and beverage are a focus for the owners, great dining is a priority with weekend cookouts, pizza baked in an authentic pizza oven flown in from Italy, and fresh oysters from their onsite oyster farm run by Oysterponds Shellfish Co. Restaurant options include Eddie’s, their beachfront eatery; a retro snack bar that offers house made pastries, sandwiches, and expertly brewed coffee; and Nookie’s, a renovation of the property’s original 1950s diner, which will be completed by fall.
Hotel Moraine also made its big debut in Greenport this summer. Formerly the Sunset Motel, this completely renovated property, by the same owners of the rosé-exclusive Croteaux Vineyards in Southold, is done up in an airy modernist beach house design that nods to the barns and farmhouses in the area. Situated on over three acres of rolling lawn and private beach, the 20-guest room resort also features a spacious lobby lounge; a communal cottage that houses a game room and outdoor bar; and a heated saltwater swimming pool overlooking the Long Island Sound. The luxe hotel offers a relaxed, family-friendly atmosphere with seasonal activities like ice cream socials, classic movies and bocce ball on the lawn, fireside s’mores, and complimentary bicycles and paddle boards. The striped umbrellas on its pebbled beach will almost make you feel like you're in one of those tranquil spots along the French Riviera.
Opened last spring, The Shoals in Southold epitomizes the peninsula’s maritime culture. Located on a marina on Peconic Bay, the 20-suite waterfront hotel houses 20 boat slips, making it accessible by both land and sea. The upscale beach motel-like property is decorated with a mid-century modern, coastal aesthetic throughout. For a fun dining option, The Shoals’ food truck parked on the waterfront lawn alongside picnic tables serves shrimp, lobster rolls, salads, sandwiches, and more from Southold General. Guests also have the option to request a tote bag full of snacks and wine from the gift shop and charter the hotel’s vintage Chris-Craft boat for a day out on the water.
Also in Southold, RICA Bath + Body owner and holistic clinician, Dr. Kristina Ivy, debuted her newest rental bungalow Lake, Sand + Sound in 2022. A mix of boutique hotel, cozy home, and serene spa, these digs are sure to please the wellness-seeker and interior-design lover alike. The 1940s lakeside bungalow—which features an outdoor shower and converted shed for in-suite spa treatments, yoga sessions, and meditation—is decorated in the same style that the RICA storefront in Greenport is loved for, with furnishings, body products, and linen robes from the brand to create a serene space where guests can rest and reset. With two bedrooms, one-and-a-half bathrooms, a full kitchen, and a living room, the house comfortably accommodates up to four guests. Private wine tastings with a local sommelier, a personal chef, and groceries provided upon arrival make your stay extra special.
While Shelter Island was originally a favorite summer retreat for old-money families and notables like Marilyn Monroe, Arthur Miller, and the Kennedys, hoteliers are now turning the tucked-away island into a year-round destination. The Chequit, owned by the same family that recently reopened Peconic Bay Vineyards, reopened last summer after a two-year renovation—just in time to celebrate its 150th anniversary. The hotel’s makeover includes a luxe update to its existing 19 guest rooms, an addition of 16 more, plus a revamp of their famed restaurant The Tavern, now overseen by chef Darren Boyle, formerly at Salt, another notable restaurant on the island. Two new food concepts were also introduced: Weakfish, specializing in New Asian cuisine and Asian-inspired cocktails; and Heights Café, which offers coffee and pastries until mid-afternoon.
The island’s iconic resort, The Pridwin Hotel and Cottages, reopened last July after its own extensive two-year restoration. The property’s full facelift gave the vintage hotel a spirited overhaul while maintaining its spirit of the good old days—it now has a luxe summer camp feel tinged with Dirty Dancing nostalgia. Situated along Crescent Beach overlooking the Peconic Bay, the waterfront hotel is made up of 33 expanded guest rooms and 16 private cottages, complete with warming fireplaces, on almost 10 acres of property. The main house features a full-service spa, a restaurant offering indoor and outdoor dining, and lots of attractive spaces to convene with family and friends. Tennis, yoga on the lawn, kayaking, and stand-up paddle boarding will keep you busy—or, if busyness is what you’re trying to escape, let attendants pamper you at the beach-view pool. Plus, weekly cookouts and s’mores over the campfire add to the summertime vibe. But the fun here isn’t reserved just for the warmer months. The 96-year-old property will be celebrating its second holiday season this winter with decked-out halls and a calendar full of festive cheer.
