East End Eats: A Gastronomic Goldmine

Greenport has been known for shipbuilding, oystering, whaling, commercial and recreational fishing, and, lest we forget, plenty of bootlegging and rumrunning
Although the fate of Claudio’s dock is uncertain and hip new stores and eateries have opened, the Greenport carousel remains an institution. Laura Donnelly

The poet Walt Whitman was a frequent visitor to Greenport because his sister Mary Elizabeth Van Nostrand lived there. He described it as a “handsome situation” that was “unsurpassed for health.” He must have been eating a lot of oysters!

Greenport is a one-square-mile village within the town of Southold. As of the latest census (2013), the population was a little over 2,000. It was originally known as Greenhill because it was a marshy area with a hill where the Greenport Yacht and Shipbuilding Company now stands. The hill was leveled and the earth used to fill in the marshy spots. In recognition of the fact that it really was a working seaport, the name was changed to Greenport in 1831.

Throughout its history, Greenport has been known for shipbuilding, oystering, whaling, commercial and recreational fishing, and, lest we forget, plenty of bootlegging and rumrunning. It was the first village in Suffolk County to establish its own electric power plant, and the Long Island Rail Road arrived in 1844. All of these milestones were cause for celebration, and the citizens of Greenport loved a good party. Still do.

Fast forward to the present day, and what is Greenport Village? It’s a little bit Williamsburg, Va., and a little bit Williamsburg, Brooklyn. Where else can you find a year-round carousel near a blacksmith shop and a camera obscura, one of only five in the country? A few blocks away you will find the Industry Standard Bar serving roasted bone marrow with “strong herbs,” pork belly bahn mi, Korean fried chicken rice bowl, over 20 beers on tap, and a $5 burger. A few more blocks away is American Beech, located in Stirling Square, in a 19th-century horse stable. It is a charming restaurant and bar with guest rooms. Here you will find Crescent duck wings with tamarind glaze, seared scallops with yellow squash puree, and buttermilk fried chicken.

Stirling Square has a few more treasures worth exploring. Check out Basso Ciccheti e Specialita, a tiny wine bar serving cured meats carved on a flywheel slicer along with cheeses, breads, and olives. You can even enjoy your glass of wine outside by the fire pit in colder months. Across the courtyard, near the ancient beech tree, is 1943 Pizza Bar, opened by the fellas who bring you mobile pizza parties in their 1943 International truck known as Rolling in Dough. Made to order in their wood-burning oven, these pizzas are the best I have ever had outside of BAR in New Haven or Al Forno in Providence. They even have BAR’s famously delicious, but weird sounding, mashed potato pizza. I opted for a special of the day, braised radicchio with speck. And wait, there’s more! Right nearby, and run by the same folks, is the subterranean speakeasy Brix and Rye, a dark-gray room where classic cocktails like Sazeracs, Trader Vic’s Mai Tais, and gin gimlets are a mighty fine aperitif before you tuck into that pizza.

As an aficionado of Greenport Village and all it has to offer, I will share my route and routine for when I visit. As soon as I get off the ferry I make a beeline for Beall and Bell, one of the more unique and affordable antique shops in a big ol’ building on Main Street. Most of their stuff is mid-century, and most of their customers are designers who scoop up the goodies and charge their clients oodles more for their unusual finds. Across the street is the Times, a funkier vintage store with old board games, toys, Playboy magazines, clothing, and an impressive vinyl collection. 

By now I am getting thirsty and hungry. If you are going to do what I do, have a designated driver! Hop in the car and head over Kontokosta Winery, just a few miles down North Road. They forbid limousines and buses, therefore there are no obnoxious bridezillas or Real Housewives-of-Wherever in sight. The 17-acre vineyard and winery are perched on a bluff overlooking Long Island Sound, and the award-winning “green” tasting facility is as beautiful as the cabernet franc is delicious. 

Then I head back into town to the North Fork’s only bookstore, Burton’s. I love this place because it is huge, the carpeting is sad, and the cookbook and local lore sections are worth browsing for hours.

In the 1920s the actor William Gillette lived in a houseboat in Greenport Harbor. His houseboy (shouldn’t that be “boatboy?”) would take Gillette’s cat for walks around the village in a baby carriage. At one point, on Front Street, there was a glamorous restaurant called Steve’s Vienna Restaurant where Douglas Fairbanks and Mary Pickford were regulars. The first submarines and torpedo boats were built and tried out nearby until the operation was moved to Groton, Conn.

During World War II, celebrities including Kate Smith and Lily Pons would christen minesweepers in the harbor. When a famous lady wasn’t available, high school girls were recruited to break champagne bottles over the bows of the new ships.

The prosperous (and smelly) days of massive oystering and catching of menhaden are over, but Greenport remains a charming, low-key, yet festive and funky village. Claudio’s has been sold so it is not known if it will remain as a favorite chowder and beer-swilling spot on the water. There are a few downtrodden-looking buildings like the Arcade Department Store but there’s also Bruce’s Cheese Shop, sushi and Latin restaurants, the fun and tasty Lucharitos Taqueria and Tequila bar, and the marvelous Frisky Oyster and Noah’s. You can get down and dirty at the Whiskey Wind bar or spend a comfortable night at the Harborfront Inn. A good sampling of the culinary treats the village has to offer can be had during the fifth annual Greenport Shellabration (www.shel labration.li) on Dec. 3 and 4, a restaurant walk featuring $5 small plates and $3 pours of local wine and beer from noon to 4 both days.

In summer there are tall ships to admire, in winter there’s an ice skating rink right next to the indoor carousel, both walking distance from the North Ferry. You will see few upscale boutiques and very few real estate offices dotting the main roads. Hallelujah!

So if you’re in the mood for a change of scenery, a sip of local wine, some delicious food, and a glance at some lovely Victorian architecture, take the short ferry rides to Greenport, the little village that remains “a handsome situation.”