The best gay bars in Boston

There is never a dull moment at this South End nightclub and restaurant—and it’s been this way since 1983. With Karaoke Wednesdays and Drag Race Fridays as part of its regular programming, Club Café proves it’s the place to be any day of the week. The restaurant, with its distinctive conservatory overlooking Columbus Avenue, serves lunch, dinner and Sunday brunch. Guests often stick around for some fabulous piano-accompanied cabaret or venture over to the venue’s dance floor for a night of clubbing. Aside from regular programming, there’s a series of special happenings each month, so check their events calendar for the most up-to-date guests.

There’s only an exclusive list of places in The Hub that offer live music seven nights a week, and Jacques’ Cabaret is one of them. Tucked alongside cute row houses at the back of Tremont and Stuart Streets, this intimate Bay Village icon has a divey, insider-like quality to it. In addition to nightly entertainment featuring drag kings and queens, and cabaret, there’s also weekly karaoke for those who want to show their stuff. Because Jacques’ is in a residential neighborhood—a very tolerant one, clearly—there’s a midnight curfew. But don’t worry; you will have packed a lot of living into the night already.

Open since 1987, Midway Café is one of Boston’s more established LGBTQ hotspots, topping locals’ and out-of-towners’ lists as an iconic entertainment destination. Located in Jamaica Plain, the nightclub hosts bands and dance nights, including its longstanding Queeraoke every Thursday, one of the city’s longest running queer nights. Neighborhood-goers also revere this dive bar’s live music scene, so this no-nonsense spot is happening no matter which night of the week it is.

This casual gay sports bar is straight inclusive, creating a friendly atmosphere to hangout with friends and family. Enjoy a bar-themed menu that includes crowd pleasers like wings, fish tacos and veggie spring rolls—or brunch classics as well as late day snacks served on Sundays. As for cocktails, its specialty creations don’t necessarily fit the typical “pub” vibe—like the Ketel One Basil Gimlet or Pinnefusion Martini—which we love! For the warmer months, the patio is the place to be, with disco music mixing with patrons’ cheers and creating a lively atmosphere. Meanwhile, the cooler months are more fitting for a round of pool or darts indoors.

Another South End staple, Trophy Room offers a friendly atmosphere, elevated pub fare and mark-your-calendar-worthy events throughout the year. It’s a more low-key kind of place during the week (although Trivia Thursdays throws in a little sassy competition), but weekends feature events like Glam Brunch Bingo and Drag Race All-Stars, which liven up the place even more than usual. The restaurant specializes in classic American fare, like burgers and a spicy chicken sandwich, while the cocktails are a little more unique, with saucy-named signature drinks like Trophy Wife and The Naked Experience.

When some local foodies hear dbar, they might associate it with its sister restaurants, Boston Chops and Deuaxve—but the local LGBTQ+ scene knows that it’s also a place to stay long after the shrimp cocktail and steak have been served. This is particularly true when the Dorchester spot hosts its weekly themed nights, like its Show Tunes Tuesdays, which feature lively sing-alongs, Pop Rocks Karaoke every Friday, as well as Slay Saturdays and Sunday Tea Dances. We recommend making a reservation for dinner and watching as the restaurant evolves into a vibrant nightlife scene on one of these special evenings.

Nestled inside Downtown Crossing, near what is unofficially Boston’s wild weekend drinking district, this long-standing, bear-centric, leather bar offers dance, karaoke and trivia nights, as well as pool tables in a casual, sports bar-like atmosphere. The entrance is a little off the beaten path, but the name is a staple among the LGBTQ community, so once you’re there, you’ll know that you’ve arrived at the right spot. The bi-level space is constantly a buzz, packing in the crowds that always accumulate on weekends (and, when in season, the weekly communal RuPaul’s Drag Race viewing parties).

The Dot’s unpretentious watering hole hosts DJs spinning top 40 tunes every Thursday through Sunday, when they also serve up a menu of pub grub. While the first Sunday of each month translates to a brunch paying homage to pop icons, the second and fourth are all about disco. Other weekly events not to miss: Friday Feels, RuPaul’s Drag Race and Mayhem Saturday.