Before the train arrived in 1844, Greenport had been already been growing up around its waterfront for some 200 years. A rare, natural, deep-water harbor between Peconic Bay and Long Island Sound became the point from which hundreds of ships were launched. Greenport today is rediscovering that waterfront with places to walk, eat, and stretch out.
Although people complain about Greenport’s being overrun now, too, it remains somewhat off the regular visitor trail, if only by just a little. Greenport tempts visitors to linger after their day of touring North Fork vineyards, with its many restaurants and bars.
Most South Forkers arrive by ferry from Shelter Island. It’s pleasant to enter the town and have your first look around from the water side. A sidewalk leads along the shore, from where the North Ferry puts in toward a huge walk-in camera obscura, which itself is just steps away from the interesting Village Blacksmith Shop, with its working forge, where decorative hooks and other handhewn souvenirs are sold. A restored antique carousel in a new weather-protected building is open seven days a week during the summer, with $2 rides.
Facing Greenport Harbor and Shelter Island Sound you can find one of the pioneers of the revitalizing waterfront, Little Creek Oysters, in a former bait shop with a view of the docks. Ian and Rosalie Wile, themselves oyster farmers, opened up about five years ago as a shuck-your-own joint. They operate the place year round, serving as many as a dozen varieties a day, often with the oyster growers themselves pitching in to open them.
Inside there is room for about 15 people at a communal table and a few stools around the bar. One bar stool is reserved for a regular who years ago worked at the bait shop and has made it a part of his routine ever since.
In winter, Mr. Wile hosts record nights, intimate listening sessions fueled by drinks and fresh oysters at which guests provide the vinyl. The rule is that a whole side has to be played; younger patrons used to the never-ending musical kaleidoscope of digital streaming are sometimes shocked to hear an entire album. It’s a new concept to them, Mr. Wile said.
Most of the restaurants of Greenport, as well as the stores, are set back from the docks, facing one another along Front Street and Main Road. It is as if Greenporters had enough of the sea in their daily lives and purposely built their downtown a ways back on dry land.
Just up Carpenter Street is Greenport Distilling and Bar, where a bright copper still — visible through the open door on sunny days — produces small batches of spirits, from spiced rum to gin.
Just outside of town, the Kontakosta Winery is the easternmost vineyard in New York State. Unlike many of the wine mills elsewhere on the North Fork, Kontakosta is deliberately low-key. Its owners, Michael and Dina Kontakosta, decided a few years ago to ban tour buses, large groups, drunken louts, and limousines. The couple also run the 35-room Harborfront Inn overlooking Mitchell Park and the antique carousel, which can serve as a hub for a multiday stay of wine tastings and poking around the North Fork’s other idiosyncratic hideaways.
Greenport is not entirely about booze and bivalves, though.
The shops are anchored by the venerable Preston’s, a ships chandlery that still stocks everything from decorative, carved lighthouses to 200-pound cast-iron mooring anchors. Newer stores display artisan glasswork and furnishings. And, if you must, there are a few places where Greenport logo sweatshirts and hats can be had.
Down near the train station, across the street from a pizza place, the American Legion now houses a sparkling new roller rink, where for $10 you can rent skates and circle away the afternoon. Officially it’s the George D. Costello Memorial Skating Rink, in honor of a post member who pushed through a long fund-raising and construction process that was derailed for a spell by Hurricane Sandy in 2012. Mr. Costello died about a month after the storm flooded the building and never got to see his beloved restoration become a reality.
The rink has a well-stocked pro shop on premises for those who want to make a commitment. Afternoon sessions tend to be kid-packed, but some evening hours are for those 21 and over, so it’s worth checking the schedule before you go.
For lunch and dinner, some visitors swear by the Hellenic Snack Bar and Restaurant for its Greek cooking, a few miles out of town on Main Road near East Marion. Close to the waterfront is Lucharitos, a Mexican restaurant that is nearly always full and buzzing. Crazy Beans on the Corner of Front and Main is great place for a late breakfast or filling lunch.
Southold, of which Greenport is a part, got its start in September of 1640, when a group of English planters arrived via the New Haven Colony. Southold likes to say it was the first English settlement in New York, which is not quite true (Lion Gardiner took title to his Isle of Wight the year before, and Southampton’s first English people showed up in June of 1640, beating Southolders by three months). Still, the history of the place runs as deep as other, more ballyhooed towns on the East End.
Greenport used to be cast as second fiddle behind its South Fork cousins, and it embraced that role happily. Being number two has had its advantages, some residents say, like keeping the boutiquization of its commercial center at bay. There are rumblings of change. Investors from out of town have been quietly snapping up commercial sites in the last few years.
The off-season is when Greenport is at its best. Recognizing this, the community has put its arms around an annual maritime festival, to be held this year on Sept. 21 and 22, with sailing vessels and artisans’ demonstrations to explore, live music, and dozens of food vendors.
The consensus from South Fork residents about Greenport is, “Shh!” — an understandable desire to keep a good thing on the down low. Not to worry, this onetime backwater on Peconic Bay is bustling but definitely hasn’t lost its soul.