Have you sampled the nightlife in Greenport? Indeed, the historical village so popular with day-trippers has plenty to offer after dark — and the scene stays lively even after summer winds down. Walk the streets and you’ll stumble on hot spots hidden (sometimes intentionally) in or behind buildings still standing from the 1800s.
INFO: 111 Main St.; 631-477-0627, claudios.com
It's hard to declare a two-acre hospitality spot "hidden" -- especially since it's been in business since 1870. The spot has recently seen some renovations and additions; the main restaurant, waterfront seating and airy Crabby Jerry's grill remain, but have been joined by Baccano Pizza by Nino, which serves up a variety of slices and pies until as late as 2 a.m. on Fridays and Saturdays. The venue's beloved dock-length bar remains, but its old awning is gone--now upgraded to a fresh covering that can be retracted when the weather calls for it--and as before, it's situated just right to catch harbor breezes and sunshine. Here you'll find day parties and nightlife (expect a cover charge Saturday nights after 9 p.m.). "I do love the history of it," says Mairead Murphy, a 47-year-old blogger from Babylon, "and I used to come here with my family. Now I come with my friends. It's legendary, it's on the water, it's got a great view, and I tend to meet interesting people here . . . it's charming."
Up Stirrs at Claudio's
INFO: 111 Main St.; 631-477-0627
Yes, this is on the Claudio's site, but it has quite the independent streak. Slated to stay open year-round and past midnight most nights, this cocktail lounge is on the second floor of Claudio's, above the restaurant. Climb a flight of stairs to enter a space with sparse decor--but as it provides amazing views of the harbor and the bustle down on Main Street, there's always plenty to look at. The bar serves more than two dozen cocktails crafted with local ingredients by Beverage Director Brian Sassen (pictured); look for options like the "Coconut 4 Way" (coconut aged rum, toasted coconut syrup, toasted coconut flakes, coconut water ice cube) and the "Miami Unicorn" (mexcal, passion fruit, lime, ginger beer, vanilla). They don't serve food-- BUT--if you're up in Up Stirrs and hungry, you can have pizza from Baccano Pizza by Nino (anything they serve) delivered to you; just text them (718-974-2040) your order and you're good. Expect DJs and live music weekend evenings.
INFO: 314 Main St.; 646-359-0463
Brand new in Greenport, this upscale bar and bite stop only opened in mid-June 2019. It features a pub section and a living room-like area with comfy couches inside, while outside there's a large patio with lots of seating that sits under a strand of dim bulbs. Like much of the nightlife in the village, it's not easily spotted; the courtyard is well hidden behind high hedges and has no sign (once on the property, you'll see a "314" over the door). The cocktail menu offers a selection of shaken and stirred options, as well as cocktail flavor "boosts" that include seaweed, wasabi, black garlic, tandoori masala, sriracha and more. Champagne and wines are also available by glass or bottle; there's low ABV (low alcohol content) and spiked slushy drinks as well.
Little Creek Oyster Farm & Market
INFO: 37 Front St.; 631-477-6992, littlecreekoysters.com
At Bootlegger’s Alley near Mitchell Park, follow the narrow little street around to the back and you’ll find a small restaurant with an even smaller bar, plus a courtyard with picnic tables. Its structure was once the cabin of a ship, since repurposed as a year-round opportunity to hang out, eat oysters (including learning how to shuck your own), grab a beer and even play games. Blake Dowling, a 44-year-old Greenport native and shop owner, says, “What they’ve created, it’s good for the summer crowd and for locals. You can come here, even bring your kids.”
INFO: 300 Main St.; 631-477-5939, americanbeech.com
Head to Stirling Square, a passage between buildings decorated with strings of bulb lights, to the back end of a former carriage house that now serves as an inn with an upscale New American restaurant. Popular with the night crowd: a courtyard featuring couches, a fireplace and a bar constructed around a real tree. Hotel guests and casual patrons mix it up here, moving between the patio and a second, indoor bar and the dining area.
Brix & Rye
INFO: 308A Main St.; 631-477-6985, brixandrye.com
Look for a weathered doorway marked by a carriage insignia. Never mind the old windows, dark vestibule with candles and a vintage shuffleboard table — the main fun is in the basement. Head downstairs to a narrow speak-easy that serves a frequently changing menu of craft cocktails and beer. Weekends evenings often extend well past midnight; closed Wednesdays. (Pictured: bartender Evan Bucholz of South Jamesport.)
Lucharitos Taqueria & Tequila Bar
INFO: 119 Main St.; 631-477-6666, lucharitos.com
It's a busy bar and restaurant with decor dedicated to images of wrestlers and a drink menu including creative margaritas, mojitos and sangria. Watch on Saturday nights for a dance party that runs between 10 p.m.-1 p.m. featuring pop hits from the ‘80s and the ‘90s.
INFO: 477 Main St.; 631-477-6782, stirlingsake.com
More than a dozen sakes and other Japanese-based beverages and food, there’s a patio, indoor bar and dining space that shows animé movies on the rear wall. (Pictured: Yokohama gyoza filled with pork and vegetables.)
First and South
INFO: 100 South St.; 631-333-2200, firstandsouth.com
A cozy, friendly pub serving upscale comfort food plus live music on Tuesday nights and pig roasts on Mondays.