36 Hours
36 Hours on the North Fork, Long Island
On the North Fork of Long Island, glasses are clinking to 50 years since a young couple planted the first commercial vines in the region. Today, with more than 40 North Fork vineyards producing award-winning merlots, sauvignon blancs, and cabernet francs, the 30-mile-long peninsula at the eastern end of the island, in New York, is also abuzz with new women-owned businesses: There are sustainable seafood restaurateurs, second-career farmers sharing their love of oysters and quahogs, innovative gallerists and pioneering winemakers finally uncorking dreams of their own. At any time of year, you can easily explore the area over a weekend. But in late fall, the crowds have ebbed, the beaches are mostly empty, locals are savoring the autumn harvest, and the crisp mornings feel ripe for an outdoor adventure along the timeless waterfront.
Recommendations
- Borghese Vineyard & Winery looms large on the site of Long Island’s founding vineyard, providing generous wine flights and an art gallery.
- Poppy & Rose is a new female-owned boutique winery with a patio on which to enjoy sauvignon blanc and apple cider doughnuts.
- Glory provides tours of Peconic Bay on an electric-powered boat, offering local history, stunning scenery and a chance for kids to take the wheel.
- Inlet County Pond Park has a perfect short hike that begins at the North Fork Audubon center and ends at the beach.
- Orient is a beautiful hamlet in which to ride a bike. Visit farm stands like Sep’s, eat crepes and dumplings at Opties and Dinghies and get spectacular views of Peconic Bay and Long Island Sound.
- VEME Studios is on a mission to make art more accessible, offering drop-in classes for abstract art, candlestick-making, figure drawing and painting your own clothes.
- Custer Institute and Observatory is Long Island’s largest astronomical observatory, where locals gather on Saturday nights to see celestial features like the rings around Saturn and craters on the moon.
- Southold Indian Museum highlights the Native American narrative with a collection that includes ceramic pots, 11,000-year-old projectile points and wampum jewelry from the Fort Corchaug archaeological site.
- East End Seaport Museum chronicles the region’s storied maritime history and runs a Saturday-evening cruise to the famous Long Beach Bar Lighthouse, known colloquially as Bug Light.
- Anker draws regulars with an inventive locavore menu and a European vibe, as does its next-door wine bar, Alpina.
- Little Fish puts a new spin on classic seafood dishes in a vibrant space near the beach.
- Minnow at the Galley Ho raises the bar on sustainable seafood and waterfront dining.
- Brix & Rye slings creative cocktails with a speakeasy vibe, as well as delicious pies from the upstairs 1943 Pizza Bar.
- Bruce & Son is a popular all-day brunch spot, serving killer egg sandwiches and great coffee from the North Fork Roasting Company.
- Coffee Pot Cellars has a winning blend of good wine, sustainability initiatives and art.
- Meadowlark is a new winery from Macari Vineyards that makes small-batch wines in a dreamy pastoral setting, and is home to popular Friday-night pizza parties.
- Aldo’s is a Greenport coffee institution with a prime location near waterfront attractions like the antique carousel and a public camera obscura with 360-degree views.
- Salumeria Sarto has become the new darling of Greenport’s Front Street eateries, serving specialty sandwiches, artisanal meats, cheeses and fabulous focaccia.
- Ray is an exquisitely curated shop with Matisse prints, Murano glass and retro-style North Fork travel posters designed by the owners Michael Aron and Nola Lopez.
- Alex Ferrone Gallery shows striking photography, paintings and mixed-media works by artists from the region and beyond.
- Willoughby is a new art salon that doubles as a refuge for artists and art lovers at the Vine + Sand bed-and-breakfast.
- Nova Constellatio Gallery is an open studio packed with landscape art by the contemporary realist oil painter Isabelle Haran-Leonardi.
- Zey Hotel is an artsy 10-room boutique hotel in Greenport with a garden, complimentary bikes and a continental breakfast. Doubles start from around $350.
- Silver Sands Motel & Beach Bungalows breathes new life into an iconic 1950s property, featuring 20 design-conscious motel rooms, 15 beach shacks and bungalows, a restaurant and bar, complimentary bikes and 1,400 feet of secluded beach in Pipes Cove. Double rooms start from around $200.
- A Walk in the Woods B&B offers charming accommodations and peaceful woodsy hiking trails just a five-minute drive from Cedar Beach in Southold. Doubles start from around $290.
- For short-term rentals, options abound throughout the North Fork. Consider a guest cottage steps from the town of Southold, or one within walking distance to vineyards in Cutchogue.
- The North Fork is a mostly car-dependent region; Greenport, however, is a small, walkable town with a Long Island Rail Road station, and the Hampton Jitney bus makes 16 stops throughout the North Fork. The South Ferry (from $3) offers a short scenic ride across Peconic Bay to Shelter Island. Dan’s Bike Rental will deliver a hybrid bike, helmet, lock and basket anywhere from Mattituck to Orient. And if you can’t decide on a designated driver, Vineyard Vans is a reliable transportation company.
Itinerary
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