A Charming Seaside Village In New York Offering Gorgeous Wineries And Waterfront Views

From the majestic Adirondacks to the bright lights of Manhattan, New York State boasts an impressive list of places to see and things to do for every type of traveler. And although many of its visitors tend to flock to the same well-known destinations — like New York City's top-rated attractions and the roaring waters of Niagara Falls — there's a quiet seaside town that's slowly become a favorite for travelers hoping to escape the crowds.

Tucked away on Long Island's North Fork, Greenport combines the best of coastal charm and wine country vibes to create a refreshing alternative for anyone hoping to experience a slower-paced seaside escape. Unlike its more glamorous neighbor on the South Fork, the Hamptons, Greenport is more about casual authenticity than high-end luxury, winning visitors over with its laid-back atmosphere, historic waterfront, and thriving food and drink culture.

Originally a bustling whaling and shipbuilding port, Greenport has transformed itself into a vibrant destination that perfectly balances its long-running maritime heritage with the best modern-day comforts. Today, the village draws in visitors year-round who are hoping to explore its historic district — which features over 250 preserved buildings dating back to the 1750s — as well as discover the local wineries, tuck into platters of fresh seafood at local eateries, and enjoy a healthy dose of retail therapy at the independent shops lined along the waterfront.

The heart of Greenport is centered around Mitchell Park, which serves as a direct pathway to the town's waterfront. That said, it's also the perfect spot for an afternoon well-spent breathing in the salt air and watching fishing boats drift in and out of the harbor. Oh, and while you're there, make sure you don't miss a stop by the park's 1920s restored carousel, though be aware that at the time of writing, the carousel is temporarily closed due to repairs, with no reopening date scheduled yet.

Outside of downtown, wine lovers will be happy to hear that the North Fork region has earned its reputation as Long Island's answer to wine country. Brimming with family-owned wineries and tasting rooms, Greenport's wine culture is booming — a celebration of local vintners, sustainable practices, and innovative winemaking. Plus, with over 20 local wineries to choose from, you'll be sure to find your perfect pour. The town's winery directory is a good place to start if you're hoping to plan your own tasting route. Alternatively, Viator also offers several Long Island wine tours that'll take you around to some of the area's most celebrated vineyards.

As for food lovers, the village offers plenty of options to enjoy some mouthwatering local grub: from shucking your own oysters at Little Creek Oysters to grabbing tacos at the vibrant Lucharitos or enjoying waterfront dining at PORT Waterfront Bar & Grill (note this restaurant closes for the winter season). Once you've had your fill, end your day on a sweet note with a visit to the Blue Duck Bakery Café or Pip's Café and Provisions. There's also the nearby Snowflake Ice Cream Shoppe that offers unique flavors and a 1950s-style ice cream store.

All this talk of wine, oysters, and ice cream got you dreaming of a trip? Thankfully, getting to Greenport is relatively easy no matter where you're departing from. From NYC, head 90 miles east (about a 2.5-hour drive) along Interstate 495 to reach the town. Alternatively, you can also hop aboard the Long Island Rail Road from Penn Station, or take the Hampton Jitney bus for a comfortable three-hour journey. Meanwhile, if you're coming from New England, the Cross Sound Ferry connects New London (Connecticut) directly to Orient Point — which is located just minutes from Greenport.

Accommodation-wise, visitors to Greenport will also be spoiled for choice. A few top-rated options include: the Soundview Inn (from around $200 a night), which offers premium waterfront views of the Long Island Sound, as well as access to a private beach and outdoor pool perfect for summer stays; Stirling House Bed & Breakfast (from around $250 a night), boasting a more intimate setting and located just steps from the village center; and the American Beech Hotel (from around $180 a night), a boutique hotel, bar, and restaurant that brings the magic of historic downtown inside.

Lastly, in terms of choosing when to visit Greenport, you'll be happy to know that the town offers year-round entertainment, which makes it an ideal destination no matter the season. However, if you'd like to avoid peak crowds, springtime or fall are both great options. Better yet, these shoulder seasons also coincide with key events like the Maritime Festival in September and the flowering of cherry blossoms in spring — two local traditions that can't be missed.