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Plane Jane
Photograph: Courtesy Plane Jane

The best drag brunch and shows in Boston

These spots serve up brunch, dinner and drinks with a side of glam

JQ Louise
Edited by
JQ Louise
Written by
Cheryl Fenton
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With dazzling makeup, enviable contouring, lavish locks and all of the glamor that their sexy looks could possibly serve, Boston’s drag divas are ready and more than willing to put on a performance for you. They’ll strut their stuff, lipsync like queens and add a ton of sparkle to any outing—whether it’s during a casual brunch with the girls or an evening out on the town. These drag shows and drag brunches around Boston hit the spot for fabulous entertainment—and some come complete with sips and snacks. For other entertainment without heels and feather boas, check out the best comedy clubs in Boston—and be sure to scope out the best brunch in Boston and the best breakfast in Boston the morning after.

RECOMMENDED: Guide to the best restaurants in Boston

Time Out Market Boston
  • Restaurants
  • Fenway/Kenmore

Every Sunday, our resident host, Plane Jane, will take the stage starting at 7 pm. The games will begin with a drag performance to kick off the hour-long bingo bonanza. Between rounds, guests can also expect appearances from fellow queens and prizes for bingo winners. It’s totally free to participate, so grab some food, some booze, and a bingo card, and hunker down for a night of fabulousness and fun. Schedule:

• 6 pm: DJ Takes the Stage
• 7 pm: Drag Performance to Start the Game
• 7:10 pm: Rounds Begin
• 7:30 pm: Drag Performance / Intermission
• 7:40 pm: Rounds Continue
• 8 pm: Final Performances

Top drag brunches in Boston

  • Bars
  • Cocktail bars
  • Beacon Hill
  • price 2 of 4

History relays the story of Carrie Nation, a radical leader of the temperance movement (the battles against alcohol in pre-Prohibition America) known for attacking barrooms with a hatchet.  Drag Me to Brunch, a weekly Sunday series held at the eponymous, 1920s-inspired Beacon Hill cocktail lounge, would be right up her alley—minus the hatchet. Hosted by Destiny Boston and Dee Dee de Ray, and featuring rotating performers, this is one of the OGs of Boston’s drag brunch scene. Brunch is served buffet style, and there are photo ops aprés-show with the performers.

  • Bars
  • Back Bay
  • price 2 of 4

One of Boston’s most beloved LGBTQ+ clubs, Club Café is a gay-friendly cabaret/piano bar/dance club/classy New American bistro. So it’s no shock that this hot spot on the edge of the South End is popular for its drag performances. Every Monday evening, the club hosts Drag Bingo with Mizery and special guests The Sisters of Perpetual Indulgence and the Imperial Court of Massachusetts. There are cocktails, a full menu, prizes and certainly memorable performances.

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  • Bars
  • Quincy Market
  • price 2 of 4

Built in 1795, the Bell in Hand is known as the country’s oldest continuously operating tavern. Today, the pub trades in powdered wigs for purple and pink ‘dos as local drag queens Kris Knevil, Teasaboo, Amanda Playwith and Karisma Geneva Jackson-Tae perform alongside special guests during its monthly Brunch of Queens. Thankfully, the food buffet setup translates to fewer server-related interruptions for the ladies.

  • Restaurants

This quirky spot in Salem transforms into fabulous on Sundays for Diamond’s Dine-In Drag Brunch. More of a super late lunch (it runs from 3pm to 6pm), this weekly event hosted by local lovely Miz Diamond Wigfall frequently has special guests (hello, local drag king Dick Kayin and Buster Pants) and always has amazing numbers, games and mimosas all afternoon.

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  • Bars
  • Bay Village
  • price 3 of 4

Say “drag” in Boston, and Jacque’s Cabaret is usually the first place that comes to mind. What’s your pleasure—Drag Karaoke, Drag on Broadway, RuPaul’s Drag Race viewing parties, Drag Comedy open mic? This longtime institution has it all (that is, except for brunch), and beauties like Destiny, Dee Dee de Ray, Crystal Crawford and Amanda Playwith  all have your attention.

  • Restaurants
  • Tapas
  • Dorchester

If there’s one place where things can get a little spicy, it’s a drag brunch—and the Tipsy Tea Brunch and Dinner Drag Queen Shows are no exception. Held at noon and 4pm, the two-hour show is everything celebratory and festive—the decor, the queens, Mexican and Latin-inspired food, and cocktails (the Tipsy Teas signature classic or flavored margarita, Hocus Pocus, and Tickle Me Pink are served in teapots). The iconic trio is Linda Marie Possa, Chanel the Angel and Candace Persuasion, but guest drag queens occasionally grace the room.

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  • Restaurants

Nestled right in the corner of historic downtown Salem, this hip, industrial-style bistro not only serves up snacks, mains, and cereal-based cocktails, but they pair those with a side of serious glam during their occasional Sunday drag shows. Mizery hits the stage with her crew by her side, as you sip on mimosas and order brunch items from the kitchen.

  • Restaurants
  • Greek
  • Back Bay
  • price 3 of 4

The Verykoko Brunch Series at Krasi offers up an authentic Greek celebration with Greek music, dancing, plate smashing and, of course, plenty of meze and cocktails. The festivities are hosted by the lovely Phaedra Phaded, and themes vary from month to month, occasionally celebrating divas like Cher, Britney Spears and more.

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  • Restaurants
  • Italian

At first glance, this intimate restaurant in Reading Center is simply a suburban go-to for enjoying Italian fare. But once a month, Venetian Moon amps up the big city vibe and turns into a raucous show of gorgeous queens winding their way table-side. Strut is held every third Thursday of the month and is hosted by Dee Dee de Ray and Destiny. Doors open at 7:15pm, with the two-hour show starting at 8 pm. While you might be tempted to just book seats for the show, don’t discount the authentic menu (and mile-long martini list) here. To arrive earlier for dinner, call ahead to make sure your table’s ready.

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