Take advantage of fewer crowds, cozy dining, and Long Island spirits. 

By Nicole A. Taylor
Updated March 28, 2019
Mark Sagliocco/Getty Images

During the sunny months in the picturesque Eastern seaboard, the perks are tangible. Warm-to-the-touch boardwalks and swaying table umbrellas sing songs of relaxation. But even during the early spring off-season, harbor town getaways hit high notes. Greenport, New York is the supreme destination for cuddled-up lodging, home grown wine, and world-class meals, and while many village waterfront dining options are on hiatus, word-of-mouth promotion keeps business steady, with fellow shopkeepers bolstering North Fork Roasting Company CBD lattes, The Halyards’ Peeko Oysters, and 8 Hands farm grass-fed lamb.

Greenport is a two-hour car or private bus ride from Manhattan and accessible by MTA Long Island Rail Road, and the North Fork—or the geographic far-right tip of Long Island—is increasingly the place where culinary fanatics go to play. Long Island’s East End is a sumptuous landscape of wineries, vegetable and fruit farms, and elevated blue plate restaurants, as chefs and makers are pushing boundaries outside of the traditional culinary circles.

On Main Street, Bruce and Son's lunch menu offers mushroom lattes, Vietnamese egg cream, and grilled gem lettuce, options that blend the latest "it" things with North Fork bounty. For an afternoon snack or coffee break, Aldo Coffee Company has the espresso shots. Staffers are roasting beans in the front portion of the clapboard house-turned-cafe, and a line streams out near a retail section of neatly wrapped hazelnut biscotti. A stone’s throw away Salamander’s On Front gourmet marketplace, which is the destination for grab-and-go lunches, on-premise-baked cookies, and friendly smiles. The year-round general store's wooden cold beverage storage and check-out counter is stacked with chef-driven sodas, Pok Pok Som, and crispy North Fork brand chips.

The Long Island Wine region, similar to California’s Napa Valley and known as grape growing land. The Area is home to over 50 distinguished winemakers. Hunkering down in a tasting room minus the free-flung bustle is the move.

“When you go to the wineries, you have a shot of getting to speak with winemakers and hear what it’s important to them. The off-season is a creative time,” says Leslie Merinoff, owner of Matchbook Distillery, a 38,000-square-feet space producing botanical-forward alcohol batches, Days Like These bar, and Lin Beach House. Local boutique retailer Spirited Wine & Liquor, along the main drag in Greenport Village, stocks Liebs Cellars, Shinn Estate Vineyards, Woffler, or Channing Daughters, and you'll find a selection of hard to find mezcals, too.

The former Shady Lady house, now Lin Beach House flawlessly weaves the Danish coziness movement into Greenport brackish air. Multi-hyphenated Leslie Merinoff orchestrated soft guest room interiors leads to crescendos at her speakeasy. The intimate hotel opened nearly a year ago, followed by the bar. Attention to detail and a selective wine list with only Macari and Jamesport Vineyards adds value to the hygge-decorated gathering spot, located on the first floor of the Victorian-style mansion.

“We choose to work with Jamesport for our dinners because of minimal intervention, really light or no pesticides, and sulfur. We are trying to support and encourage local agriculture to become organic or even biodynamic as possible. Also, we make a beer with Greenport Harbor Brewery, and the only ones served,” says Merinoff.

The cylinder vases, illuminated with candles, set the mood for the communal experiences for vacationers. Airbnb takes a portion of the small-town rental inventory, but Lin’s ongoing pop-up dinner series fosters community among chefs and guests. Paw Paw, a “North Fork-inspired ‘pop up,’” has put out a BBQ duck spread, featuring kelp butter for dipping and duck egg sundaes for dessert.

“The only rule is no talking about work or politics,” explains Merinoff. The 10-seat experience is available during every season. Building a soundtrack is a bit easier, with an ever-so-thought-out respite, glasses to clink, and plates to clear. Choosing budding cherry blossom shorelines and straight from the farm grub always plays well together.