A Food and Wine Lover's Guide to the North Fork

Long Island — the snake-tongue sliver that juts out from the bottom of New York — is, as they say, a land of contrasts. On the western end, my end, you have the densely populated boroughs of Brooklyn and Queens. In the middle, tight city blocks give way to lawns and suburban sprawl. Then, everything gradually thins out until you reach land's end: two spindly peninsulas, separated by the five miles of Peconic Bay. The famous one is the so-called South Fork, home of the Hamptons. The other one is different.

The North Fork has long been wilder, more isolated. While elsewhere on Long Island Olmsteds were planning urban oases and Whitman was writing about ample hills, it remained a land apart. Historically, those who have lived here — the indigenous Corchaug, seafaring English colonizers, whalers and clammers, and itinerant farmers — have made their living off land and sea. A two-and-a-half-hour drive from Manhattan, the area was not entirely undiscovered by vacationers once New York City began to expand outward. But gentrified, it was not.

In recent years, though, boutique hotels, craft cocktails, and more than a few transplants from the city have brought increased attention to the North Fork. Still, a connection to land and sea remains — and locals want to keep it that way. On a brisk Thursday night in October, I headed east to see how the enterprising community is keeping the spirit alive.

Friday

I woke with the sun at the Sound View, just outside the town of Greenport. Built in 1935, this is the platonic ideal of an old-school seaside motel, with sun-bleached wooden buildings stilted over the water along a private beach. It's also an emblem of the change that has recently come to the area. After a 2016 purchase, the property's 55 guest rooms were given the requisite millennial update — subway-tiled bathrooms, pine-paneled walls — from design firm Studio Tack (now Post Company) and Eagle Point Hotel Partners, the team behind Greenport's Harborfront Inn. But the Sound View has also become a gathering place for North Forkers, who stop by year-round for Long Island wines and creative cocktails.

I migrated to the lounge and ate my continental breakfast by way of Brooklyn: chia-seed pudding, house-made cereal bars, and La Colombe coffee. I know 20 people in the city who would move here tomorrow, I thought as I watched the steely waves of Long Island Sound, waiting for my friend Ben to arrive for plus-one duty. I hope that doesn't happen.

One way people are maintaining local roots in the North Fork is through the terroir. With Ben in tow, I ventured out for a tour of Bedell Cellars, a 40-year-old vineyard and winery in nearby Cutchogue. Founded by Kip and Susan Bedell, it's now the domain of winemaker Richard Olsen-Harbich, who is something of a walking encyclopedia of North Fork viticulture. Over a juicy glass of Petit Verdot, he explained that this is one of the youngest wine regions in the U.S. When the area was planted, back in the 1970s and 80s, it didn't have the best reputation. "The tendency back then was to copy California," he said. "But this land is actually a lot like the Loire Valley or northern Italy."

Vintners started consulting with their counterparts abroad, eventually pivoting to grapes like Sauvignon Blanc and Cabernet Franc. Now, Olsen-Harbich says, "We're growing with a lot more precision and information and care." He also helped develop the guidelines for the Long Island Sustainable Winegrowing consortium. Twenty-two members, representing half the acreage of the region — including premier North Fork operations like Kontokosta Winery and Rose Hill Vineyards — have been certified for their environmentally friendly approach to soil health, irrigation, and pest control. "We're starting to become our own person, so to speak."

Ben and I returned to the Sound View, each with a few more bottles of Blanc de Blancs than we had intended to buy, in time for our dinner reservation at The Halyard. Like the rest of the hotel, the restaurant rests on stilts over the shore; the dining room is paneled in dark wood in the style of an ancient whaling ship.

We ordered a crudo of meaty fluke, delivered that morning from the Southold Fish Market and layered with green apples, and a salad of lettuces and crunchy radishes sourced entirely from nearby KK's the Farm. The wine list, too, stays close to home. I sipped a 2018 white Merlot, citrusy and floral, from Bridge Lane in nearby Mattituck as I looked out at the sound, which surrounded us in all directions.

Saturday

The sea was still on our minds as we headed a couple miles east to Greenport and the East End Seaport Museum, a cabinet of nautical curiosities housed in an old train depot. The docent, Althea Burns, walked us through the treasures: rusted harpoons, sailing-club pennants, heirlooms from the Floyd shipping family who made Greenport into a regional hub. My favorite was the huge Fresnel lens, built in the 19th century, that once lit up Bug Light, a nearby lighthouse — the museum offers lighthouse boat tours May through October. Boating here is truly in people's blood, Burns told us; during World War II, North Forkers patrolled the surrounding waters for German U-boats in their own repurposed vessels.

For lunch fresh off the boat, we walked a few doors down to Claudio's, a Greenport seafood institution founded by a whaler from Portugal in 1870 and listed on the National Register of Historic Places. Though it changed hands after nearly 150 years of continuous family ownership, by all accounts Claudio's is still Claudio's: you eat crackly Montauk calamari and lobster dipped in melted butter, while gregarious staffers drop by every so often with a crumb scraper and a Bloody Mary refill. Stephen Loffredo, who co-manages Claudio's with his business partner, Tora Matsuoka, told me the restaurant has long been a part of the formal and informal economy of the area. On top of supporting local fishing, he said, "bootleggers used to row up and deliver booze through a trapdoor in the bar."

These days, a decidedly legal operation can be found a short walk away at Matchbook Distilling Co., where Ben and I met cofounder Leslie Merinoff for a tour and blending workshop. At the time, Merinoff, a Brooklyn émigré, had just come from the Lin Beach House, the boutique hotel and cocktail spot she owns in town. She greeted us with a pour of North Fork watermelon eau de vie before instructing us on how to craft our own spirits using locally grown botanicals like lemongrass and coriander.

"A lot of young food and beverage professionals are moving here," Merinoff told us as we walked through her laboratory-like space, where she mills her own grains and grows koji, a rice mold she adds to her whiskey instead of malt. In Merinoff's experience, the way for newcomers to integrate into the North Fork ecosystem is to work with the people who are already there. "I love doing experiments with small farmers," she said. "This year, we were able to grow our own ingredients and do everything biodynamically." Matchbook is a community distillery, meaning individuals and businesses can make small batches, too; the Halyard has partnered with Matchbook on its proprietary gin, which captures the North Fork with notes of lavender, apricot, and seaweed.

That evening, we headed west to dine at North Fork Table & Inn, a standard-bearer of North Fork cuisine set in a historic country home near Southold. Founded in 2005 by James Beard Award–winning pastry chef Claudia Fleming and her late husband, Gerry Hayden, it's currently helmed by chef John Fraser, who recently unveiled a renovation and menu revamp. Fraser honors the founders' original vision, drawing inspiration and ingredients from the surrounding farms, vineyards, and waters. On a chilly autumn night, a local Pinot Noir and plate of Parisian gnocchi with rabbit ragoût was exactly right.

Sunday

We stopped for one last glass of wine at Mattituck's Macari Vineyards before making our way back to the city. The award-winning winery excels at pushing the North Fork envelope: its biodynamic approach involves herds of donkeys and Longhorn cattle, and unusual bottles include the tart Early Wine, inspired by Austrian Jungwein, made from grapes harvested a few weeks ahead of schedule.

But Macari is perhaps best known for its Bergen Road red blends, produced exclusively from the North Fork's best vintages. I sipped the 2010 Bergen Road — spicy, supple, and perfectly autumnal — as I watched a sea mist roll over the vines. From where I sat on the breezy patio, during that sweet window when fall is just about to round the corner to winter, vineyard and pasture were all I could see.

A version of this story first appeared in the November 2020 issue of Travel + Leisure under the headline "All Points East." The Sound View provided support for the reporting of this story.