Part of the Gay Boston Guide — bars, events & things to do.
Boston, Massachusetts
Cocktails and American plates inside the South End's Staypineapple.
Trophy Room is the restaurant and bar inside the Staypineapple hotel at the corner of Berkeley and Chandler, in the heart of Boston's South End, the city's historic gay neighborhood. It runs all day, from breakfast through late-night weekend cocktails, with an all-American menu of shareable plates and a cocktail list built around house drinks like the Recover Mary. Operating under the tagline 'a place for everyone, love is love,' it leans into its queer-friendly South End address rather than treating it as incidental. The crowd is a mix of hotel guests and neighborhood regulars, and the room sits more on the polished-bistro end of the spectrum than the dive-bar one, which makes it a good daytime or pre-night anchor before the Tremont Street bars get going. Weekly drag programming adds a reason to linger past dinner.
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Weekend breakfast from 8am.
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