With its local wineries, bucolic pastures, farm-to-table food scene, and oyster-abundant coast, Long Island’s North Fork feels worlds away from New York City. In reality, though, the sweet seaside region is approximately 90 miles from Manhattan.

For weekenders more interested in relaxation than ritz, the North Fork is the ultimate getaway. The peninsula’s largest town, Greenport, offers a laid-back alternative to Long Island’s flashier summer escapes like Montauk and the Hamptons. Boutique shops and laid-back eateries line the 19th-century village’s downtown avenue, and the roads that connect Greenport to the North Fork’s nearby towns are dotted with family-owned farm stands and vineyards. Here’s how to enjoy a blissful escape from the city on Long Island’s North Fork.

Where to stay

The interiors of Sound View Greenport’s 55-guest rooms are inspired by modernist beachside homes.
Once an iconic 1950s motel, Sound View Greenport is a design-lover’s dream spot by the sea. Recently revamped by Eagle Point Hotel Partners and Brooklyn-based design firm Studio Tack, the 55-room waterfront property blends classic motel motifs with a nautical New England twist. Situated along a quarter-mile stretch of the Long Island Sound, the area’s freshest seafood is a mainstay on the menu at the property’s restaurant, The Halyard.

The ocean-facing lobby lounge at Sound View Greenport looks out on the Long Island Sound.
At Sound View Greenport, a poolside bar called Jack’s Shack serves lobster rolls and boozy Popsicles made of local lavender, and on-property activities include yoga and meditation by the sea. Spend your morning sipping freshly roasted La Colombe coffee at the hotel’s divine ocean-facing lobby lounge, and don’t miss the hotel’s piano bar, where a partnership with Manhattan’s iconic Joe’s Pub brings intimate performances by up-and-coming musicians to the space every weekend. (Rates start from $325 per night this summer.)

Closer to town but farther from the shore, other stylish Greenport stays include American Beech, a former horse stable turned hotel with a farm-to-table restaurant (from $295 per night), and The Lin Beach House, an intimate, check-yourself-in-and-out guesthouse featuring its own cocktail bar, Days Like These, where you can sip custom-blended gins and botanical-infused spirits from Matchbook Distilling Company, a recently opened craft distillery in Greenport. (Each room at The Lin Beach House is listed separately on Airbnb and starts from $350 per night.)

Where to go winetasting

Long Island’s terroir has drawn comparisons to France’s Bordeaux region and the Napa Valley in California due to the fact that the wine countries sit on approximately the same latitude. But Long Island’s saltwater sea breezes and moderate temperatures give the North Fork’s wines their own unique zest, and to sip the best of them only requires a quick trip around the peninsula. Kontokosta Winery in Greenport is the North Fork’s only waterfront winery. Featuring 62 acres of coastal farmland, this family-owned sustainable vineyard includes a wind-powered tasting room, which is open to the public seven days a week.
Macari Vinyards is located near Greenport in Mattituck on Long Island’s North Fork.

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The nearby towns of Mattituck and Cutchogue are also abuzz with some of the region’s finest wineries. In Mattituck, taste wines and munch on Neopolitan-style, wood-fired pizzas served from Avelino, the gourmet food truck at the family-owned Macari Vineyards. The Macari family started making wine in the ’30s and ’40s in the basement of their home in Queens, New York. Today, the family runs this 500-acre vineyard that produces award-winning wines (tastings for $30 per person).  

In Cutchogue, visit Castello di Borghese Vineyard and Winery, Long Island’s oldest vineyard opened in 1973. Lieb Cellars, known for its reserve pinot blanc, and McCall Wines, renowned for its pinot noir and merlot varieties, are also notable stops.

What to do

Beyond the Long Island Wine Trail, day-to-day North Fork activities include leisurely bike rides, boat tours, and farm excursions. Outside Greenport, Cutchogue’s 8 Hands Farm is an absolute must-see. The 28-acre family-run farm sells fresh eggs from pasture-raised hens at its on-site market, where you’ll find hand-woven rugs and knitted clothing made using wool from the farm’s Icelandic sheep. The sustainable farm also features an outdoor food truck that serves breakfast and lunch from a seasonal menu.

For a day on the water, call Peconic Water Sports, Long Island’s leading water sports company located in Southold and Sag Harbor (with pickup service on Shelter Island). Charter a boat, take a fishing tour, rent a kayak, paddleboard, or Jet Ski, or simply cross the Peconic River to Shelter Island—whatever you do, this staff of boat-loving experts will ensure you enjoy the adventure.

During the summer months, head east of Greenport to East Marion for a peek at one of the country’s largest lavender fields, Lavender by the Bay. Wander through 17 acres of blooming lavender, then shop for a variety of aromatic products at the farm’s on-site store. (For visitors over 12 years old, entry to the fields costs $9 per person on weekends and national holidays and $6 per person on weekdays.)

The Times Vintage in Greenport, Long Island
The North Fork has a shining reputation for its creatively curated vintage shops, many of which are located in downtown Greenport. At LIDO you’ll find design-forward clothing, jewelry, accessories, and home furnishings sourced from fair-trade artisans around the world. The Times Vintage, housed the former office of the Suffolk Times newspaper, includes a superb selection of vintage clothes, vinyl records, and home furnishings. On Front Street, the North Fork Art Collective showcases local art for sale in a welcoming streetfront exhibition space, and the lifestyle boutique Tea and Tchotchkes offers a unique array of one-of-a-kind bags, scented candles, plants and pots, essential oils, and clothing.

Where to dine

In downtown Greenport, enjoy flourless matcha pancakes or a grass-fed beef burger at Bruce & Son, an all-day brunch café on Main Street. For lunch, head to Little Creek Oyster Farm & Market to shuck your own oysters (selections change daily) while sipping local beers from Greenport Harbor Brewing Company.
Squid ink risotto at Barba Bianca
Don’t miss dinner at Barba Bianca, Manhattan chef Frank de Carlo’s waterfront restaurant situated right on the harbor in downtown Greenport. The nautical-inspired dining room features a seasonal menu that boasts coastal-Italian delicacies, all focusing on ingredients sourced from within a five-mile radius of the restaurant.

Other celebrated farm-and-sea-to-table restaurants in Greenport include the Noah’s, the Frisky Oyster, The Halyard, First and South, and PawPaw, a pop-up restaurant helmed by chef Taylor Knapp—who previously cooked at Copenhagen’s highly regarded Noma—serving a seasonal “supper” menu on select Saturdays (reservations required).

Getting there: 

  • Hampton Jitney Inc. offers daily service to the North Fork with pickups in Manhattan; $20 each way when booked online. The trip duration is approximately three hours (without traffic).
  • Long Island Rail Road offers daily service to the North Fork from Penn Station in Manhattan and Atlantic Terminal in Brooklyn; $30 each way when booked online. The trip duration is approximately three hours and 20 minutes. 
  • By car, take Interstate 495 East (the Long Island Expressway) and follow directions to the North Fork. The trip duration is approximately two hours and 20 minutes (without traffic).
  • From Connecticut, take the high-speed Sea Jet Service from New London to Orient Point on Long Island; $21.50 each way. Trip duration is approximately 40 minutes.

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