Local wineries. Bucolic pastures. Farm-to-table food scenes. Oyster farms up and down the coast. Long Island’s North Fork, feels worlds away from the hustle of New York City, though it’s only 90 miles and a couple hours (traffic gods willing) out to the northeastern peninsula.
Its largest town, Greenport, offers a laid-back alternative to Long Island’s flashier summer escapes like Montauk and the Hamptons. Vintage shops and independent restaurants 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.
With an influx of new hotels and restaurants popping up, there’s always something new to check out as well as classic spots to revisit. If days spent oyster slurping and wine sipping sound like your idea of a perfect escape, here’s a guide to help plan a weekend getaway on the North Fork of Long Island.
Where to stay on North Fork, Long Island
Silver Sands Motel and Beach Bungalows, a ‘50s landmark waterfront property in Greenport, reopened with a modern makeover in June 2023.
Photo by Paul de Luna
Silver Sands Motel & Beach Bungalows
Walking into the Silver Sands lobby is like stepping into a Wes Anderson film set. Every detail from the newly reopened Greenport motel tells a story, from the painted-shell room numbers to its vintage seahorse neon sign. Originally built in 1957, the motel’s retro peach-and-teal color palette and mid-century modern decor pay homage to another era. But a makeover completed earlier in 2023 brings this landmark North Fork motel into the 21st century, complete with a smaller footprint and ethical design, while still staying true to its nostalgic roots.
Sitting on 1,400 feet of private sandy beach facing Shelter Island, the motel has 20 guest rooms, and 12 different-sized beach bungalows. Chef Ryan Hardy, known for Manhattan restaurants Charlie Bird and Pasquale Jones, is one of the co-owners and at the helm of the motel’s beach restaurant Eddie’s. The menu nods to Hardy’s Italian repertoire but with the unfussy vibe of the North Fork; think wood-fired Neapolitan pizza topped with Littleneck clams and oysters plucked fresh daily from Pipes Cove, which is just a swim away from your dining table. (Silver Sands owns and helps maintain 15 acres of private underwater land in partnership with Oysterponds Shellfish Company.)
A nod to the farmhouses of North Fork, Hotel Moraine’s barn-like lobby has a grand fireplace, lobby bar, and sundries shop.
Photo by Doug Young
Hotel Moraine
Opened in summer of 2023, this family-friendly resort offers expansive views of the Long Island Sound from its perch on the bluff of Harbor Hill Moraine. With three acres of rolling lawn and private beachfront, the 20-guest room resort feels like a super-luxe farmhouse escape with its communal cottage which doubles as a game room and bar, firepits and saltwater pool. Daily experiences, from movies on the lawn to arts and crafts for the kids, will occupy everyone in the family without leaving the resort.
Located in the center of Greenport, the Menhaden has the only hotel roof deck in North Fork, where guests can watch sunsets and roast s’mores over firepits.
Photo by Doug Young
The Menhaden
If you want to be in the center of town and walking distance to the ferry and docks, the Menhaden is a great choice. Built in 2018, it’s located on the former site of one of Long Island’s first hotels, the Peconic House. With only 16 rooms, this boutique hotel feels as personal as it gets, with fresh breakfast pastries and housemade cookie nightcaps delivered to your floor’s 24-hour accessible galley, which is also complimentary and stocked with ice cream and local goodies. You’re only a text away from the digital concierge which will bring wine and s’mores up to the rooftop—the only North Fork hotel to have a roof deck—where firepits and harbor views await. With a prime location on Front Street, you can easily get around by borrowing one of the hotel’s loaner bikes or getting a ride from the hotel’s electric Moke.
The Lin Beach House
The Lin Beach House is 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 craft distillery in Greenport which also offers a “create your own gin experience”. Each room at the Lin Beach House is listed separately on Airbnb and starts from $300 per night. Check out Edie’s Room, Jane’s Suite, and Debbie’s Room.
The interiors of Sound View Greenport’s 55 guest rooms are inspired by modernist beachside homes.
Photo by Read McKendree
Sound View Greenport
Another former ’50s motel, Sound View Greenport’s modern makeover was courtesy of design firm Studio Tack and Eagle Point Hotel Partners. The 55-room waterfront hotel, set on a quarter-mile stretch of the Long Island Sound, mixes New England modernist with coastal minimalism (think crisp, clean lines everywhere).
The area’s freshest seafood is a mainstay on the menu at Sound View’s restaurant, the Halyard. For drinks, head to its poolside bar called Jack’s Shack or grab an Adirondack chair in the sand at reservations-only Lowtide Beach Bar. After a restful night, start your morning sipping freshly roasted La Colombe coffee at the hotel’s divine ocean-facing lobby lounge.
American Beech
Closer to town but farther from the shore sits the stylish American Beech Hotel, a former horse stable turned hotel with a farm-to-table restaurant. It’s a great option for guests who want to be within walking distance of the town’s restaurants, bars, and boutiques, set in Greenport’s historic Stirling Square. Dog parents: Good news, this place is also pet friendly.
Where to go wine tasting on the North Fork
Long Island’s terroir has drawn comparisons to France’s Bordeaux region and the Napa Valley in California because all of these 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 appeal, and to sip the best of them only requires a quick trip around the peninsula. Here are the towns—and the best wineries—to go wine tasting on Long Island’s North Fork.
Greenport
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.
Photo by Sarah Buder
Mattituck
In Mattituck, taste wines and munch on charcuterie at the family-owned Macari Vineyards. The Macari family started making wine in the 1930s 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.
Cutchogue
In Cutchogue, visit Castello di Borghese Vineyard and Winery, Long Island’s oldest vineyard (though it only 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. Meadowlark North Fork opened in 2022 as the new sister property to Macari Vineyards, focusing on biodynamic and organic farming methods. Peconic Bay Vineyards reopened in 2021 and hosts oyster happy hours on Fridays, and private picnics overlooking 148 acres of vines.
Things to do in North Fork, Long Island
Beyond the Long Island Wine Trail, day-to-day North Fork activities include leisurely bike rides, boat tours, and farm excursions. Below are some of the best things to do in North Fork, Long Island.
Locally grown and hand-harvested in Southold, Founders Oysters are “best served and slurped in the natural brine.”
Photo by Doug Young
Oyster Cruise on Vintage Yacht
Cruise around the North Fork eating fresh oysters in a restored 1936 Chris Craft yacht. Founders Oysters farmer Steven Schnee offers private cruises onboard his vintage 31-foot wooden yacht, The Half Shell. You’ll boat over Schnee’s underwater oyster farm while slurping on oysters and sipping local North Fork bubbly. Schnee tells you everything you want to know about Nork Fork oysters, including how to shuck your own in style.
Visit 8 Hands Farm
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 handwoven 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.
Fish, kayak, paddleboard, or jet-ski with Peconic Water Sports
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.
Visit Lavender by the Bay’s lavender fields
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.
The Times Vintage in Greenport, Long Island.
Photo by Sarah Buder
Explore Greenport’s vintage stores
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. Housed in the former office of the Suffolk Times newspaper, The Times Vintage includes an impressive selection of vintage clothes, vinyl records, and home furnishings. On Front Street, North Fork Art Collective showcases local art for sale in a welcoming street-front exhibition space. Tea and Tchotchkes sells one-of-a-kind bags, scented candles, plants and pots, essential oils, and clothing.
Where to eat in North Fork
In downtown Greenport, start your day off with hotcakes with fresh maple syrup 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.
A new sustainable seafood restaurant in Southold, Minnow at the Galley Ho, is making a splash on the dining scene with its environmentally conscious focus. From only using line-caught local seafood and local produce to its refurbished and reclaimed wood furniture, thrifted silverware, and returnable glass-to-go containers, your dinner will taste even better knowing it’s helping this coastal area thrive.
Other celebrated farm-and-sea-to-table restaurants in Greenport include 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).
The best way to get to the North Fork from the tri-state area
From Manhattan, hop on the Hampton Jitney, with daily direct coach bus service to North Fork, with numerous stops including Greenport. The trip takes approximately two and a half hours, depending on which stop.
Long Island Rail Road offers daily service to the North Fork from Penn Station in Manhattan and Atlantic Terminal in Brooklyn. 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 takes 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. Trip time is approximately 40 minutes.
This article was originally published in 2020; it was updated on September 8, 2023, with current information.
