The Berkshires generally rolls up its sidewalks early. The area’ s daytime charm, accented by hike-able hills and a smorgasbord of cultural attractions, typically gives way to quieter, star-lit nights. But for those who crave a little more light after dark, a few local spots buck the early curfew and offer an oasis for night owls.
B y T a y l o r S t a u b a c h
An Insider ' s Guide to the Late-Night Scene
A scene with Johnny Irion and company at the Lion ' s Den.( Courtesy of The Red Lion Inn)
The Berkshires generally rolls up its sidewalks early. The area’ s daytime charm, accented by hike-able hills and a smorgasbord of cultural attractions, typically gives way to quieter, star-lit nights. But for those who crave a little more light after dark, a few local spots buck the early curfew and offer an oasis for night owls.
Just off Church Street in downtown Lenox, Ombra buzzes with energy until 1 a. m. The cozy 32-seat restaurant serves inventive dishes, popular birria tacos, and its signature Millionaire Tots until midnight. Guests can choose from a rotating list of featured cocktails and an extensive selection of wine and craft beer. Named“ best small town bar in Massachusetts” by Thrillist, Moe’ s Tavern in downtown Lee is known for its craft beer tap list( their website is nocoorslight. com), as well as its extensive whiskey selection. With a BYOF( bring your own food) policy, Moe’ s is open until 11:30 p. m. seven nights a week. For dinner before drinks, pop in to The Locker Room Sports Pub before the kitchen closes at 9 p. m. for a large selection of favorite pub dishes. Stick around until 11 p. m. Tuesday through Thursday and midnight Friday through Sunday, for rotating entertainment like trivia, music bingo, and a variety of local music talent. The hilltowns are humming if you know where to look. Venture off the beaten path to the Shaw Pond Club located on Otis Road in Becket. Karaoke, darts and live music punctuate the week— open until 11 p. m. Monday through Thursday and midnight on Fridays and Saturdays. Papa Bob’ s Place, also in Becket, is open until midnight Monday through Saturday. A hidden gem with over 200 Google reviews, the restaurant and bar serve pub favorites until 8 p. m. Offering traditional bar food in a welcoming atmosphere, stop at Papa Bob’ s for bingo, karaoke, bar games like flip cup and pong, live music, and more.
Great Barrington boasts a number of late-night options, including the comfortable and laid-back Miller’ s Pub on Main Street, with light fare options like Biff’ s Garlic Buffalo Wings to complement a cold beer until 11:30 p. m. on Fridays and Saturdays. In the mood for masterful mixology? Head over to Mooncloud on Railroad Street for outrageously creative cocktails and mocktails alongside curated full-sized dinner“ tagliere”( charcuterie) boards until midnight on Fridays and Saturdays. The newest venture of Thistle & Mirth owners Austin Oliver and Joad Bowman, Lucy’ s Rendezvous is popular with the night owl crowd— for those that can find it. Located in the alley that connects Main Street with The Triplex parking lot, and open seven days a week until 1 a. m., Lucy’ s has a speakeasy vibe for those in the know. In Stockbridge, the historic Red Lion Inn hides more than one secret inside. In the hotel’ s basement, The Lion’ s Den swings into the night with live jazz on Wednesdays and Sundays and a rotating lineup of other live music later in the week. Order a seasonal cocktail or mocktail like the“ Buzzless Brew,” settle under the iconic crimson tin ceiling, and feel transported to the Gilded Age until the clock strikes 11 p. m. Over in West Stockbridge, the contemporary Italian restaurant Acqua Al 2 keeps its doors( and bar!) open until 11 p. m. Wednesday through Sunday. The recently renamed ButtonBall Barn in South Egremont delivers a different kind of vibe. Formally The Egremont Barn, this historic 1830s roadhouse hosts live music nearly every night with the bar staying open until midnight. Bands range from local favorites to touring artists, who fill the rustic space with a“ honkytonk” energy. Step into the spotlight on Open Mic Night, every Wednesday. The barn’ s massive fireplace and seasonal hot toddies keep guests warm and cozy throughout the winter. On New Year’ s Eve the Barn presents Blues Year’ s Eve with GA-20, a farewell to 2025 with a champagne toast at midnight.
64 // BERKSHIRE MAGAZINE Holiday 2023 2025