Gay sports bars, over-the-top drag brunch parties, and so much more.
The city might not be known for its LGBTQ+ nightlife or bar scene, but that doesn’t mean that there aren’t hidden gems scattered throughout Boston and nearby neighborhoods that are worth checking out. Massachusetts was the first state in the nation to legalize gay marraige afterall, so you better believe we’ve carved out a slew of bars, over-the-top drag brunch parties, and other nightlife options for the LGBTQ+ community in Boston. No matter what type of bar or night out you’re looking for, you’ll find it here—so take a look at the best queer-friendly spaces in Boston.
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Since first opening in 1987, Midway Cafe has welcomed some of the best local acts around from punk bands to soul serenades to stand-up comedy performances, not to mention their famous Queeraoke every Thursday. As one of Boston’s longest-running LGBTQ+ nights, Queeraoke breaks into a range of ‘80s to early-2000s throwbacks along with alternative, underground, and popular hits from modern day—making this spot ideal for nights when you and your posey are ready to take the stage. If that’s not enough of a selling point, the cafe also partners with local LGBTQ+ organizations for outreach, fundraising, and awareness events to increase equity and uplift the community.
Located in the heart of Dorchester, you’ll find blend, a restaurant turned nightclub with weekly dance parties, disco-themed brunches, and local drag queens (like Harlow Havoc) tearing up the dance floor and helping to get you on your feet all night long. Before you get started, peruse through their full dinner menu, offering light bites from a watermelon and feta salad to something with a bit more substance like a BBQ chicken burger to fuel your night out.
The grand dame of the LGBTQ+ scene opened in 1983 and, man, if those dark walls could talk. The $75 VIP club membership ($50 each year for renewal) grants longtime patrons free admission on club nights as well as dining discounts and an exclusive invite to the quarterly “VIP Only” cocktail receptions or wine tastings. While the Sunday brunch buffet is still the best hangover cure in the city (only $18.50!), and the $24.95, three-course weeknight dinner special is a hidden city bargain.
Although not a full-fledged LGBTQ+ bar, Carrie Nation happens to be one of the hottest spots for brunch, with a recurring Sunday drag brunch, dubbed “Drag Me to Brunch,” worth adding to this week’s agenda. If you’re not completely sold, check out the spot’s Instagram for a sneak peek. And if you’re wondering where Carrie Nation got its name from, for even more reason to swing by, the club’s name ironically stems from historical figure Carrie Nation, a radical member of the temperance movement who had opposed alcohol pre-prohibition, and went as far as destroying bars in the process. So what better way to pay homage to Nation’s failure than by launching one of the most entertaining and premier cocktail clubs in Boston?
Earning the title of Boston’s oldest running gay bar, you’ll swear you’re in the wrong place until the moment you slip inside. The tiny, well-heeled enclave of Bay Village seems like an unlikely home for the city’s best drag shows, but here we are. Seven nights a week, the showgirls of Jacque’s treat you to all manner of performative raunch, from drag karaoke to drag stand-up comedy. It’s a magnet for bachelorette parties and birthdays, sure, but also anyone aware of the cabaret’s allure or curious of what a night at Jacque’s could entail.
Cathedral Station is the answer to the question:“Where do all the flag footballers drink?” The only gay sports bar in town also happens to boast myriad appeals, from the free parking out back to the pool table inside to the enormous enclosed patio. The pub fare grants you all the classics, from wings to chicken pot pie, the massive brunch dishes are quick hangover cures (AKA “Hangover Elixirs” on the menu), and the cocktails are as crafty (and boozy) as ever.
Formerly home to a neighborhood Irish pub, dbar has transformed into a full service restaurant offering seasonal New England fare and an extensive wine list. The dishes are certainly worth the hype, with comfort food favorites including their meaty veal and pancetta bolognese—but don’t fill up too quickly because the restaurant morphs into a nightclub and lounge every night of the week, especially popular on Tuesdays, Fridays, and Saturdays. For the latest updates on their theme parties (like “Flannel Frenzy”), check out their dbar after dark Instagram for more.
Give yourself extra time to get there, because The Alley’s clandestine location requires significant sleuthing. But once you’ve discovered the hidden den, you’ve found your fellow bears. This is the place for weeknight trivia, late night beers (it closes at 2 am every night), and barely clothed dance parties. The once-grubby bathrooms got an upgrade a few years back, however the cash-only bar transactions remain.
Known for its award-winning cocktail menu and overall welcoming vibe, Trophy Room is a beyond-fun and friendly environment for those looking to sit back and enjoy a quality drink followed by dinner. But we can’t not talk about their brunch. A go-to for those in the South End, Trophy Room’s brunch serves up the standard eggs, toast, and bacon, but you can also dive into their avocado toast, breakfast pizza, or eggs benedict. Don’t forget to peruse the morning libations, featuring a spin on signature breakfast drinks like the Fritz Mimosa and Chandler Street Coffee.
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