On the northeast shore of Long Island, there is a 170-year-old maritime village that loves to be explored. Rustic pleasures, boutiques, and acres of award-winning local vineyards abound. And for the relic-seekers, a 40-foot carousel built in the 1920s. Walt Whitman and George Washington used to summer here in what remains a scenic and romantic respite from metropolitan life.
Originally founded as a whaling community, this narrow peninsula consists of beautifully restored buildings and residences dating as far back as the 1700s; many structures still intact are of Victorian, Federal, or Georgian style. A town steeped in history, in the 1840s, Greenport became a transportation hub when the Long Island Railroad was extended, making it the main rail-steamboat link between Boston and New York. In the 1920s, during the prohibition era, Greenport was known for its rum-running. Cauliflower and potato farming soon developed as a major trade, followed by an increase of restaurants, marinas, specialty shops, hotels and tourism, which added to the local economy.
In the 1970s, the Hargrave family converted local farmland into vineyards. Optimal climate and soil conditions have helped the New York wine industry flourish—particularly in Long Island’s North Fork where there are currently more than 33 local wine producers. (For more information about Long Island wines and events in the vineyards, contact the L.I. Wine Council.)
At least 15 local wineries offer daily tours and tastings, generally for a fee of between $2 and $5. Wineries and farm stands are clearly posted on Route 48 or Route 25 (Main Road). A local public bus S92 goes along the Main Road. Should you seek other means of transport within the North Fork there is winery transportation as well as local limousine service. Because the village proper is only one square mile it is unnecessary to require wheels, unless you care to rent a bicycle at Bike Stop. The North Ferry Company offers transportation between Greenport and Shelter Island. In addition, there are three taxi services, but the point is to get away from taxis, yes?
The clean air, winding walking trails, and gregarious residents serve to enrich the journey of tasting the area’s great wines. With only 2,100 residents, Greenport’s locals are relaxed and friendly, helpful with directions, and will chat informally about the town, be it about its history or the best local galleries. This place has done exceptionally well in balancing tourist-friendly amenities with local charm. You can go on a harbor cruise or stop by the local Trivial Pursuit HQ. Talk with the locals or visit Greenporter Hotel and Spa. The village has numerous antique shops, a couple of small museums, the four-acre waterfront Mitchell Park with the antique carousel, and quite a few restaurants and cafes. (Trivia: Greenport boasts the country’s oldest same-family owned restaurant—since 1870. See end of article for the answer.) Recently, and rather unfortunately, an H&R Block and a Starbucks have opened here. But thankfully, it appears the independently owned businesses are prevailing.
While only a two to three hour trip away from New York City, Greenport’s visitors tend to linger for a romantic overnight in one of the town’s delightful, cozy B&Bs. There is the Harbor Knoll Bed and Breakfast, situated a block from the Jitney/LIRR stop, with four rooms and a cottage to choose from. Guests can putter around many areas of the home, from the library, bar, dining room to the two drawing rooms. As an alternative, there is the Siren’s Song Carriage House, Stirling House Bed & Breakfast, Drossos Motel, and several others. While the above accommodations are year-round, it is a good idea to confirm with the wineries’ hours, in advance. The peak season is approximately Memorial Day to Labor Day, yet each season offers a distinct and undeniably delicious charm.
Transportation:
Hampton Jitney (212.477.1200, hamptonjitney.com)
LIRR (MTA Schedule)
Bike Stop (631.477.2432)
The North Ferry Company (631.749.0139)
Pristine Limousine Ltd. (631.871.1508)
Restaurants:
Claudio’s Restaurant (111 Main St., Greenport, 631.477.0627, claudios.com)
The Loft (48 Front Street, 631.477.3080, theloftrestaurant.net)
To Do:
L.I. Wine Council (631.369.5887, liwines.com)
Mitchell Park (631-477-2200, greenportvillage.com/mitchellpark.html)
Accommodations:
Harbor Knoll Bed & Breakfast (424 Fourth St., 631.477.2352)
Siren’s Song Carriage House (631.477.1021)
Stirling House Bed & Breakfast (631.477.0654)
Drossos Motel (631.477.1334)
Greenporter Hotel and Spa (326 Front St., 631.477.0066, greenporter.com)
How to get there: Hampton Jitney is the most convenient means of transportation to and from Greenport, with several East Side Manhattan pick-up/drop-off locations throughout the day. An accessible alternative to this is the LIRR. Both the Jitney and LIRR station is Greenport; both stops are within a stone’s throw of one another, located conveniently in the village center.
Sarah Knapp is a Brooklyn based entrepreneur whose love for the outdoors and community building led her to the October 2013 creation of OutdoorFest. She has a BA in History, is a Wilderness First Responder and a NY state hiking, camp and boating guide. Her proudest achievement to date is reading the Aeneid in Latin. 
Allison was one of our first top writers and Chief Editor but is no longer working with offMetro. Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributed travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She never missed a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. 
Josh Laskin is a freelance travel writer and photographer based in the White Mountains of New Hampshire. When he is not at work or on the road, you can find him in the mountains snowboarding, climbing, hiking, fly fishing, mountain biking, and eating bagel bites.
Annie is a travel writer, environmentalist, and surfer based in Venice, CA. She heads up our West Coast team, keeps our grammatical errors in check, and makes sure our California writers always have a plan for their next adventure. Follow Annie’s travels @annelisemcb.
Carly Pifer is a freelance writer who has been known to follow whims inspired by romantic movie scenes or colorful street style shots to India, Japan, Tunisia and Argentina. After stints living in Seoul, Boston, Paris and Los Angeles, writing and searching for something intangible, she landed somewhat steadily in Brooklyn and has begun to find inspiration in her more immediate surroundings. 
Kate E. O’Hara is a New York based freelance writer and photographer who loves all things food—especially the people who make it and market it. Her writing aims to capture the essence of the food experience; the stories that go well beyond a plate of ingredients. In addition to her love of food, Kate is also known to have a hankering for red wine and craft beer. You can also find Kate on Instagram