On the low-key North Fork, the pleasures of wine, fresh seafood, and a new luxury hotel make Greenport the getaway of the season.
1. Get Your Morning Coffee
At Aldo's Coffee Company, a small roaster and bakery helmed by gregarious Aldo Maiorana, the pours are intense, the local gossip is there for the overhearing, and the biscotti are worth every gluten-infused bite.
2. Cruise the Bay in Style
The sleek lines and jaunty striped awning of the Glory—a reproduction of an 1839 electric Fantail launch—are the ideal setting for a tour of the harbor and Peconic Bay. Even better: Glory is solar-powered, making the journey quiet and eco-friendly.
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3. Eat Oysters
With the icy waters of Peconic Bay as a breeding ground, Greenport was once the oyster-producing capital of New York. Get your bivalve religion at Little Creek Oyster Farm & Market, an artfully weathered shack on the docks where you can enjoy a fresh haul for half price (if you shuck them yourself) and pair them with the area's excellent beers and wines. Leave time to browse the market's artisan foodstuffs and oyster-inspired swag.
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4. Go Wine Tasting
Greenport is an ideal base for North Fork vineyard excursions—visit Kontokosta Winery and its high-ceilinged, barnlike tasting room, overlooking the vines in one direction and Long Island Sound in the other.
5. Try a Local Brew
It's not just all about the grape in this part of the North Fork: Greenport Harbor Brewing Co. & Tasting Room, housed inside a former fire station, offers a roster of seasonal and year-round small-batch ales and lagers on tap.
6. Shop and Ogle
As part of its ongoing reign as the town's tastemaker central, American Beech, a fashionably serene little hotel in Stirling Square, populates its reception area with an impeccably appointed boutique. Designed and curated by co-owners Brent Pelton and fashion designer Alex Vinash, The Shop at American Beech skews toward sophisticated resortwear and a few of Vinash's high-impact runway pieces.
7. Hit the Park
Mitchell Park is the village's lush little heart—all four acres of it. With one edge fronting a 60-slip marina, the park also contains two delightful (and family-friendly) amusements: an antique carousel and a camera obscura. In September, the square fills with nautical splendor as the Greenport Maritime Festival takes over with parades, boat displays, music, dancing, and outdoor movies.
8. Explore Lighthouses
Get a dose of seafaring culture on one of the East End Seaport Museum's excellent lighthouse cruises. The Bug Light Cruise & Tour includes a visit to this picturesque lighthouse, and the three-and-a-half-hour lighthouse cruise takes in four historic lights plus offshore seals.
9. Enjoy Cocktails & Pizza
The bar game has to be strong in a beach town to lure drinkers away from water views, and Brix & Rye—tucked in the basement of a former livery off Main Street—provides just that siren call. The reason? Superb classic cocktails, updated with passion and nuance by co-owner Evan Bucholz, and wood-fired pies featuring local clams and produce from 1943 Pizza Bar upstairs.
10. Do Dinner Right
The Halyard, a stunning restaurant at the Sound View hotel, has deft preparations of classics like fish-and-chips, fried oysters, and lobster sliders (plus a deck that may have the best view on the whole Atlantic seaboard). Keep an eye on social media to see if PAWPAW, Greenport's pop-up darling, is serving supper on the Saturday you're in town: The innovative pairings of fresh proteins and produce are show-stopping.
With its sandy beachfront and dreamy views of Long Island Sound, the recently opened Sound View has brought a former beach motel into the stylish present with design that dances between nostalgia and nautical mod. Plan your visit around the twice-monthly Chef's Table cooking demonstrations at The Halyard, not to mention performances and karaoke at the Piano Bar. Rates start at $195.