We take things outside in the summer months — in a non-confrontational way, of course. Who says happy hour shouldn’t follow suit? While summer is without a doubt the high season for the Hamptons, offering some of the swankiest dining options on the island, it’s safe to say the South Fork does have the outdoor eating and drinking game on lock and what’s more, the happy hour lives on at some.
If the thought of a Hamptons happy hour has you feeling ecstatic, be sure to peep some of our favorite spots that are hosting ’em. Some offer a truly outdoor happy hour experience while most have that delightfully breezy, minimally covered, inside-but-feels-like outside vibe that makes summertime sipping that much more delicious. Cheers!
Bostwick’s On the Harbor, 39 Gann Road, East Hampton, 631-324-1150
This seasonal waterfront seafood restaurant is beloved for its stunning sunset vistas, carefully crafted cocktails and seafood-centric fare. A weeknight happy hour is heavy on drink deals and the aforementioned seafood. On Mondays and Fridays from 5 p.m. to 6:30 p.m., guests can clink glasses full of $6 draft beers, $12 select house wines and $12 specialty cocktails. The sunset bar is also serving up a shrimp cocktail, Peconic oysters and a lobster roll (you’re welcome).
Springs Tavern and Grill, 15 Fort Pond Blvd., East Hampton, 631-604-6944
The one-time watering hole of painters Jackson Pollock and Willem de Kooning, which opened as Springs Tavern in 2022, has a key lime pie that once drove a former president and first lady to its property. But it’s the happy hour that banishes the Sunday scaries and draws regulars from both east and west. Every Tuesday through Sunday from 4 p.m. to 6 p.m., the tavern features indoor and outdoor bars, with the latter being a white-shingled bar complete with a beachy aesthetic and all the spirited fixings for the perfect cocktail. Potstickers, little neck clams and fried dough-filled corn fritters served with homemade horseradish sauce pair well with $12 vinos and margaritas (yes, frozen is an option). Should an evening shower force you indoors, let the ability to listen to live music soothe the summer bummer.
Sundays on the Bay, 369 Dune Road, Hampton Bays, 631-728-2611
This lively, easygoing resto is a true summertime fave for those west of The Canal. Adjacent to its older sister operation, Oakland’s Restaurant & Marina, Sundays has a sprawling waterfront deck that gives way to glorious sunset views on a year-round basis. Staying for the sunset is highly recommended, obviously, but come for the happy hour on Mondays through Fridays from 3 p.m. to 6 p.m.. Specials allow attendees to cool off with $6 beers, $10 house wines and $10 mixed drinks. While the food is regular-priced, the seafood-centric menu plays nice with the cocktails and views.
Village Bistro East Hampton, 10 Main St., East Hampton, 631-907-2772
This breezy outdoor Main Street restaurant has a coast-chic restaurant with white walls and cushy blue booths. But it’s outdoor patio combines the ability to take in an al fresco Hamptons evening with the joy of people watching, which is frankly with a glass of rose or margaritas in hand. Both are $10 during nightly happy hours, which run from 4 p.m. to 6 p.m. indoors and out. $1 oyster specials highlight a special happy hour menu that also boasts tavern classics like chicken wings and prime rib dip.
RUMBA, 43 Canoe Place Road, Hampton Bays, 631-595-3544
Accessible by boat (you can ride one from sister restaurant CowFish if you don’t have one), just sailing to this Caribbean-inspired eatery takes you to another kind of Island. Step off and find yourself greeted by a boisterous atmosphere, outdoor area and spacious rum bar. Happy hour is served from 3 p.m. to 5 p.m.. If that’s not a sign to punch out early, what is? Speaking of punch, the Caribbean rum punch made with Cruzan light and dark rums, triple sec, pineapple, orange and lime juices is a crowd favorite. And rum flights will truly take you away.
Bistro 72, 1830 W Main St., Riverhead, 631-369-3325
Happy hour at Hotel Indigo’s chic farm-to-table restaurant has an appropriately locavore feel. Tacos from North Fork Taco? They’re on the menu, including one with grilled shrimp and roasted corn that hits differently this time of year. Over half a dozen other riffs on pub favorites like loaded nachos, southern fried chicken wings and flatbread pizzas are also available. The menu is available from 4 p.m. to 7 p.m., Sundays through Fridays, except for holidays. But for an authentic al fresco feel, mark your calendar for the annually-anticipated Patio Series, which brings specials, live tunes and aesthetics to the hotel’s outdoor space. A sure-to-be-stylish Rose Garden Party follows on Thursday, Aug. 26, with fall-forward events (BBQ and Whiskey on Thursday, Sept. 26, and All Things Apple Cider on Thursday, Oct. 24) helping us transition back to cooler but cozier times.
Union Burger Bar, 40 Bowden Square, Southampton, 631-377-3323
Don’t let the name fool you. Serving a hybrid menu consisting of both signature and build-your-own burgers, hand rolled sushi and sashimi, plus familiar Mexican fare options, like steak tacos and union nachos with tastebud-rollercoaster pickled jalapeños, the five-days a week happy hour is an equally ample offering. Available from Monday through Friday from 3 to 6 p.m., guests can order $6 beers, $8 wines and $10 cocktails. Technically, deals are only available at the indoor bar, but folks can savor their sipper at one of the myriad picnic tables scattered about on the outside lawn.
