Oliwien Pakuta from Poland visits Greenport Village on Aug. 24.

Oliwien Pakuta from Poland visits Greenport Village on Aug. 24. Credit: Randee Daddona

Greenport may date back to the 1630s, but it's feeling pretty of-the-moment right now. There's flourless matcha pancakes at an all-day brunch spot, a picture-perfect waterside shack where DIYers can learn how to shuck their own oysters, and no shortage of "hidden" speakeasies shaking up bespoke cocktails.

In other words, plenty of eye-candy for Instagram.

"Great transformations happen organically and that is what’s happening in Greenport. It’s gaining momentum,” says Stephen Loffredo, operating manager of Claudio's restaurant, a landmark eatery that opened in 1870 and was owned by the same family for nearly 150 years … until it was sold last year. Although the eatery's beloved dock bar remains, a late-night pizza bar and second-level cocktail lounge have been added. Loffredo says it can be challenging to make changes to a place that's stayed so iconic for so long, but "eventually everything changes, but locals are very protective of their history and individuality. That’s what makes the mix out here so special."

While summer has always been peak season for day-trippers and vacationers, "we’re now busy year-round on the weekends," says Kassata Bollman, who opened the restaurant Bruce & Son with her husband Scott in late 2016 before renovating and reopening in 2017. She’s noticing that her customers are now a mix of locals, combined with people coming from as far as New York City.

Here are six places that embody the old-meets-new energy of the village:

Bruce & Son

WHERE 208 Main St.; 631-477-0023, bruceandsongreenport.com

WHY Brunch is an all-day, every day affair here, where the menu features dishes such as vegetarian masala toast and flourless matcha pancakes alongside twists on classic sandwiches. You can order a photo-ready Bloody Mary or oat milk and honey espresso with chocolate liqueur. Yet when the owners put the restaurant together, they held on to the building’s history — note the “Corwin’s” druggists sign in one corner, left behind by the original 1849 owners, and the sign left over from when Horton’s Ice Cream sold 20-cent ice cream sodas. “People come in here,” says Bollman, “and they look up and see we kept the building’s original ceiling, and they’re like, ‘Wow, I like that.’ We think people really appreciate seeing that when they walk in, and see these parts of the village’s history, they do really like it.”

Roasted baby summer squash, masala toast and granola paired with...

Roasted baby summer squash, masala toast and granola paired with cocktails served at Bruce & Son in Greenport on Aug. 24. Credit: Randee Daddona

Little Creek Oyster Farm & Market

WHERE 37 Front St.; 631-477-6992, littlecreekoysters.com

WHY It’s little spots like this that tell the current Greenport story. There's no signage or advertising for this tiny bait and tackle shack fashioned from the cabin of an old ship that's practically hidden down Bootlegger’s Alley near Mitchell Park. But there they are — streams of people who come to try shucking their own oysters while sampling local craft beer, with a waterside view.

The Times Vintage

WHERE 429 Main St.; 631-477-6455, timesvintage.com

WHY Nostalgia for bygone eras runs high in this 1909 building, which once served as the headquarters for the Suffolk Times newspaper. These days, this well-curated shop sells vinyl records (log any requests on the clipboard) and loads of vintage clothing, curios and home decor items including midcentury highball sets. It's the sort of spot you might expect in Brooklyn or Manhattan. Owner Elizabeth Sweigart says business is “improving every year.”  

Oysters, knives, protective gloves and hot sauce are among the...

Oysters, knives, protective gloves and hot sauce are among the tools provided to shucking students at Little Creek Oyster Market in Greenport. Credit: Aaron Zebrook

Brix & Rye

WHERE 308A Main St.; 631-477-6985, brixandrye.com

WHY All you’ll see is a dark vestibule with old windows and a vintage shuffleboard table — but go inside and head down to the “Sunrise Room” — once the basement of a livery stable dating back to the 19th-century— and it's a speakeasy where barkeeps mix up an oft-changing selection of old-meets-new cocktails with names like "Clarified Milk Punch" and "Don's Beach Planter."

Greenport Fire

WHERE 125 Main St.; 631-333-2233, feelthefireny.com

WHY Heat comes in many forms and several are sold here — hot sauces, cigars and candles. Consult the chalkboard for the current sauce offerings or browse cigars such as a hand-rolled Honduran Leaf by Oscar or the Gurkha Cellar Reserve made with 18-year-aged tobacco.


WHERE 111 Main St.; 631-477-0627, claudios.com

WHY If you've been to Greenport, you can't miss Claudio's — it's where generations of Long Islanders have made a tradition of eating, whether inside the main restaurant or al fresco at the floating dock-bar. The new owners have added fresh elements: Baccano Pizza by Nino, which offers a variety of slices and pies until as late as 2 a.m. on Fridays and Saturdays — is right by the dock entrance. Then there’s “Up Stirrs at Claudio's,” a cocktail-driven lounge on the second floor with amazing views of the harbor and an elevated drinks menu to match.

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