Your Next Weekend Escape: Greenport, Long Island

The Hamptons may be NYC’s de facto summer destination, but the North Fork has plenty to offer too—like the quaint seaside town of Greenport. With nearby wineries, a local brewery and a charming downtown, Greenport is the quintessential summertime village to spend anywhere from an afternoon to a week. Plan a trip to this hamlet at the far end of Long Island and you’ll be pleasantly surprised at how much you can enjoy out east without the Hamptons crowds (but with just as much rosé).

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welcome to the village of greenport sign
John Cardasis/Getty Images

Get There
Can’t wrangle a car for the weekend? No problem: The Long Island Rail Road stops right downtown (from $22 each way), an easy walk to nearby hotels and home rentals. The Hampton Jitney also provides service to the area, including a stop in downtown Greenport by the train station (from $21). If money’s no object (but cool factor definitely is), charter a seaplane through Shoreline Aviation to take you from Manhattan to Shelter Island.

Wander the Main Drag
The cute downtown of Greenport along Front Street and Main Road features all the small-town charm you’d expect: bakeries, boutiques, seasonally driven restaurants and lots of sidewalk seating for enjoying a midday beverage. After lunch on the patio at First and South, pick up some homemade bonbons at Hampton Chocolate Factory, stock up on hand-poured soy candles at The Weathered Barn (we’re partial to the floral hyacinth scent) and grab an afternoon snack at Greenport Creamery (a newly opened reincarnation of the 40-year-old Sandpiper). Everything is in view of the sailboats and yachts at the marina.

sound view greenport hotel
Read McKendree/Courtesy of Sound View Greenport

Stay the Night
Plenty of seasonal Greenport residents offer their homes for rent on Airbnb, so check out the platform for houses and cottages fit for groups. There’s also American Beech, a cozy, 11-room luxury hotel nestled in the historic Stirling Square (from $369 a night). It features a chic bar and restaurant as well as a fashion boutique featuring designer Alex Vinash’s resort collection. For more of a getaway feel, head out of the main village to the Sound View Greenport, a nautical-inspired boutique hotel overlooking the Long Island Sound (from $189). Here, wood-paneled walls, shiplap, rattan chairs and an underlying mid-century vibe give the hotel its character, while the food sourced from local fishermen and nightly bar music from New York artists keep it feeling authentically New York.  

Learn About Seafaring History
Educate yourself on Greenport’s maritime history at the East End Seaport Museum. With a saltwater aquarium, a collection of lighthouse lenses and exhibits explaining the area’s history as a major whaling port, you’ll leave a little more enlightened on the impact the area has had on New York. Plus, if you’re traveling with kids in tow, there’s Captain Bob’s Quarterdeck, an interactive children’s room where former science teacher Bob Jester leads hands-on activities.

little creek oyster farm
Courtesy of Little Creek Oyster Farm

Shuck Oysters
It’s time to “go shuck yourself,” or so say the owners of Little Creek Oyster Farm & Market. Housed in a former bait and tackle shop overlooking the marina, this oyster shack serves up local beers alongside a daily selection of mollusks. If you opt to shuck your own, the team will provide you with all the gear and know-how to do it. You’ll appreciate that briny flavor even more when you’ve pried the shell open yourself with a knife and a steel glove. (Though if you’d prefer to leave it to the experts, you can do that too.)

macari vineyards
Courtesy of Macari Vineyards

Taste Wine
Hire a driver from East Wind Limo and take a day to taste the wines of the North Fork; many wineries are within a 20-minute drive. Macari VineyardsPalmer Vineyards and Channing Daughters Winery showcase the best of what this New York wine region can do with grapes like merlot, cabernet franc and chardonnay. Of course, there’s plenty of rosé too. At Macari, make a reservation for a tasting on the expansive terrace overlooking the vineyards—it’s the idyllic shot you’ll want for Instagram—or hit one of the winery’s many summer events

Go Fishing
Charter a boat for a day off the coast. Challenger Charters offers half-day and full-day rates, plus all the bait, tackle and gear you’ll need. Expect to find species of fluke, striped bass, Atlantic cod and more. The staff will even fillet and package anything you catch. If fishing isn’t your thing, you can also book the captain for a boat tour of the area’s lighthouses or pack an on-board picnic and sail around Shelter Island.

greenport harbor brewing
Courtesy of Greenport Harbor Brewing Company

Drink a Beer
Yes, this village has its own brewery, and it’s pretty darn delicious. Spend an afternoon at Greenport Harbor Brewing Company and sip its lineup of ales, lagers, IPAs and more. There are two locations: The original is housed in the old jail in downtown Greenport, while the larger beer garden is a short Uber ride over to the nearby town of Peconic. Don’t leave either without tasting the Black Duck Porter.

Ride the Ferry to Shelter Island
A sleepy island squeezed between the North and South Forks of Long Island, Shelter Island makes for an ideal half-day trip from Greenport. Hop the car ferry from the marina (an eight-minute ride) for a drive around the 27-square-mile island, which features vast nature preserves, beautiful estates and plenty of history. In fact, some of its residents are fifth generation and have called the island home since the American Revolution. Pack a picnic for the beach or opt for a seafood-filled lunch at Salt on the waterfront.

brix and rye
Courtesy of Brix & Rye

Grab a Nightcap
Just because you’re outside of the city doesn’t mean you can’t get a well-crafted cocktail. At Brix & Rye, order a classic Sazerac, a barrel-aged negroni or the bartender’s choice—trust us, you’re in good hands. If a dive is more your speed, step into the Whiskey Wind Tavern, where you can guzzle a cold pint while playing billiards or one of many arcade games. There’s even karaoke on the weekends.

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Freelance PureWow Editor