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A bird’s-eye view of Greenport. (Credit: David Benthal)

Four years ago we launched an online interactive contest to see what our readers felt was the best hamlet or village on the North Fork. It was the most anticlimactic game of all time as Greenport, a heavy favorite going in, stomped everyone en route to the title. 

The North Fork is filled with hidden gems like New Suffolk and scenic wonders like Orient, but Greenport was a tall order for any community to have to go up against.

A one-time whaling port, Greenport, which was colonized in the mid-17th century, features a little something for everyone. Even as a top stop for visitors to the North Fork, the community’s enormous local pride still shines through in the way it celebrates its heritage. That’s particularly true at the annual Maritime Festival in September and through the East End Seaport Museum, Stirling Historical Society and the old jail, blacksmith and schoolhouse buildings that leave you feeling as if you’ve escaped to some other time or place.

Even as the fishing industry has died down, what remains of it is visible from Greenport’s picturesque docks and open waters, where tour boat companies like Glory Going Green and Peconic Cruise Line can take you out to breathe in the salt air and see the community from a new vantage point.

Hours spent killing time in Mitchell Park (drinking a cup of Aldo’s coffee no doubt!) also offer a prime snapshot of the village. Watch the boats dock at Claudio’s or ride the carousel as you wait for the Monday night Dances in the Park series to get underway again in July.

Foodies, of course, could spend a lifetime in Greenport and never get tired of the dozens of restaurants that combine to satisfy virtually any craving at any time of day. In this village it’s not about finding a place to eat, but rather narrowing down your options to just one. Do I want Bruce & Son for breakfast or Crazy Beans? Am I in the lunchtime mood for tacos at Lucharitos, fried chicken at Salamander’s or pizza at 1943 Pizza Bar? These are questions not easily answered.

Other popular dining spots include Noah’s, The Frisky Oyster and First & South for small plates, entreés and a drink; Little Creek Oyster Farm & Market, Port, Porto Bello and The Halyard for waterfront dining; and don’t even think of leaving town without a trip up Main Street to Stirling Sake and Brix & Rye.

Before visiting any of these or the many other fine choices along Front Street and beyond, patrol the shopping district for great finds at shops like The Weathered Barn, One Love Beach, Beall & Bell and more.

Anchor your stay by thinking outside the box with a suite at American Beech (also a first-rate dining spot),
a bed-and-breakfast like the Tapestry House or a more traditional experience at the cozy Greenporter Hotel.

And while Greenport makes its mark as a respite from wine country, the community features Kontokosta Winery, the only Soundfront tasting room in town, and Greenport Harbor Brewing Co., the North Fork’s first brewery.

Wherever your next stop takes you in Greenport, it’s hard to go wrong. Just be sure of one thing: Don’t let a visit to the North Fork pass you by without checking out this charming, historic village.