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North Fork in the Fall: The Idyllic Weekend Escape on Long Island

Less than two hours by road from New York City, a weekend on South Fork, Long Island can include trips to wineries, destination restaurants, antique stores, and outdoor activities—all of which come alive in the fall

Separated from the busy, buzzy, and more brazenly showy Hamptons by Shelter Island and the Peconic River, North Fork shows what the Hamptons might have looked like a few decades ago. While South Fork may have the glitz and the undeniable glamour, the high-profile residents and the grand estates, the quiet beauty of North Fork is no less alluring. You’ll find outstanding vineyards and farms; historic properties and excellently stocked antiques stores; and a superb range of amenities catering for a multitude of interests, be they on land or on the water; and, above all, the promise of a good life that it delivers by the bucketload.

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During harvest time, many of the wineries in North Fork, Long Island put on tastings and evening events. Image: Alice Falcone. Banner Image: Greenport, North Fork, Long Island, Getty Images.

“We fell in love with North Fork from the minute we discovered it,” says Alex Azcona who, with his partner Dan DeVito, owns South Harbor Inn—the first five-star hotel in the area. “We knew the Hamptons well, and one vacation decided to break with tradition. We took a left instead of a right where the road branches, found the peace we’d been searching for, and a place we really didn’t want to leave. We knew we needed to be here.”

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The rugged beaches of North Fork, Long Island are quieter than those of The Hamptons at South Fork, and yet just as beautiful. Image: Alamy

A Natural Paradise

“North Fork is a pastoral idlyll,” says Azcona. “And each season gives us something different—summer is all about being outdoors, exploring our coastline, and enjoying the huge range of watersports, including kayaking, paddle-boarding, and sailing, or taking a bike ride out to the lavender fields of family-run Lavender by the Bay farm.”

For many people, though, fall is the main draw. A magical time when the trees are ablaze with gold and red, and the community comes together to enjoy a range of activities such as pumpkin-picking, hayrides, and evening events at the many wineries, which will light their firepits and host wine-tastings accompanied by live music.

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Claudio's Wharf in Greenport Harbor, Long Island, is home to some of North Fork's most popular restaurants, as well as live jazz evenings on weekends. Image: Alamy.

Charming Neighborhoods

North Fork’s beguiling towns are a key attraction. Leading the way is Greenport, the unofficial capital, which was a simple whaling village in the 19th century. Today, it’s a hub of fine restaurants run by renowned chefs from New York City, chic hotels, and unique shops filled with antiques and original art. Great pickings are to be found in Lido, which sources designer vintage and limited-edition clothing and jewelry; White Flower Farmhouse, which has an exceptional collection of ceramics and European linens; Beall & Bell, where you might find an Eames chair or an industrial French bar cart; and the North Fork Art Collective, which exhibits work by local artists. Those considering a move to North Fork should pay a visit to Hadley Wiggins-Marin’s store North Found & Co. where the interior designer’s sensibilities are reflected in her covetable collection of vintage and antique decorative items and homewares.

A typical cedar-clad house in the hamlet of Orient in North Fork, Long Island. Image: Alamy

Luxury Accommodations

Picturesque Southold, in the heart of North Fork’s wine country, is also deeply alluring, and is where Azcona and DeVito chose to open their exemplary four-bedroom inn, in a 19th-century farmhouse that’s only a 20-minute walk from South Harbor Beach. “We just felt an instant sense of recognition,” says Azcona, “not only about the property, but with Southold itself. It is quieter than Greenport, but we found the intimacy of its restaurants and bars very appealing, and also received tremendous encouragement from other hoteliers and business owners. There have been quite a few new hotel openings recently, including The Menhaden and Sound View, both in Greenport, which is attracting more people to our shores.”

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The interiors at the South Harbor Inn in Long Island's North Fork combine comforts such as Frette linens and European baths with vintage and contemporary collectibles, and a bold yet elegant color palette.

A Haven for Food-Lovers

Acclaimed restaurateurs have also flocked to North Fork to head up established kitchens or open their own. Frank DeCarlo, of New York City’s Peasant, opened Barba Bianca—named in honor of old, white-bearded fishermen—in 2017, serving up what’s fresh out of the water and from the surrounding farms. This is very much a trend in North Fork, with other celebrated restaurants also putting local produce at the top of the menu. Greenport’s The Frisky Oyster, Noah’s, The Halyard, and First and South all offer from-the-sea or farm-to-table dining.

For a delicious lunch on the run, try the North Fork Food Truck, which you’ll find in the parking lot of the North Fork Table & Inn. Here, the house specials are the lobster roll, the all-beef hot dog with sauerkraut, and the Berkshire pulled-pork sandwich.

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Known as Long Island Wine Country, North Fork is home to some 30 wineries and 3,000 acres (1,214 ha) of planted vineyards. Image: Alamy

Don’t Forget the Wine…

North Fork’s wines have been compared with those of Bordeaux and Napa Valley, and though there are some similarities, the ones you’ll taste here have their own pleasantly saline character imparted by the salty sea breezes. So many of the wineries are excellent that you could almost take pot luck, but if you wanted to go with a local favorite, Azcona recommends Bedell Cellars—its 2009 Merlot was served at President Obama’s 2013 inaugural lunch. He also name-checks McCall Wines, which does splendid Pinot Noirs and Merlots, Lieb Cellars, which excels in reserve Pinot Blanc, and Kontokosta Winery, a 62-acre (25 ha) vineyard overlooking the sea, where both the 2016 Sauvignon Blanc and 2014 Cabernet Franc are also worth writing home about.