Rick Friedman/Corbis
Samantha DiMauro
October 22, 2014

The lesbian, gay, bisexual and transgender community has a lot to look forward to when visiting Boston. The South End is the most established gay neighborhood in the city, with a rich history of gay and lesbian life and home to a slew of influential and historical LGBT gathering grounds. The nightlife options range from modern meccas—like the video dance club Club Café—to more sedate classics like the Boston Eagle. Epic Saturdays at the House of Blues are run by the same masterminds behind the wildly adored Hot Mess Sundays at Underbar, and The Midway’s healthy line up of queer-friendly gatherings is quickly making it a frequent go-to haven. Every June, the Boston Pride Parade and festival douses the streets in confetti, good cheer and open hearts in a true show of color. No matter where you’re planning to go out tonight, it’s the night to be out and proud!

Visit T+L's Boston Bar Guide for more Boston bar inspiration.

Club Café

This bar is has something going on every night of the week—whether it’s trivia, karaoke, or the ever-popular Monday night Drag Bingo. Spend Saturday night dancing yourself silly at RUSH, the raucous electronic dance-music rave complete with strobe lights, smoke machines and flashing music videos projected on the walls.

The Midway

Out in Jamaica Plain, this cash-only eclectic haven is often jam-packed with a curious crowd eager to check out a diverse weekly line up of live shows. Swing by to see everything from burlesque revues to head-banging metal bands—but be sure to stick around for Thursday night’s Queeraoke, one of Boston’s longest running queer nights, and the most talked about ladies’ night in town.

The Boston Eagle

One of Boston’s oldest gay bars, the Eagle’s legendary status is well earned. Marked simply and understatedly by a stone eagle perched above the entrance, this no-frills South End dive bar is the place to go past midnight for a last-call pour and smooth conversation over a game of pool or jukebox tunes.

Underbar

Playfully under-the-sea-themed, with cool watery hues, driftwood tables and glossy sea-shell-studded walls, this bar’s two rooms fill to capacity for the ever-popular Hot Mess Sunday. Finding the entrance can be a bit tricky, but enter through the doors for Club Royale and follow your ears toward revamped versions of ‘80s and ‘90s hits.

Jacques Cabaret

Drag queens reign at this historic Boston showroom whose dark and divey veneer is just one part of its effortless charm. Opened for business in 1938, it became the starting place for Boston’s first official Gay Pride March in 1971. Come prepared with a wad of singles and your loudest laugh, sit in the front row and tip well for a chance to get noticed and pulled up on stage!

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