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.
Have feedback on this description? Let us knowWeekend breakfast from 8am.
Get the full experience — check in, follow this venue, and connect with the community.
No upcoming events
Try checking a later date or browse events in the app
Catch your city's vibe or the global LGBTQ+ scene.
No spam, unsubscribe anytime.
From the first state to legalize same-sex marriage to a walkable gayborhood in the South End, here's your insider guide to queer Boston.
June is Pride Month, and the chaos is real. Here are 25+ of the best gay events in June 2026 across North America, organized by week so you can actually plan your travel.
Your complete guide to every dedicated lesbian and sapphic bar currently operating in the US, mapped by city, with what makes each one worth the trip.
The gayest cities in America, ranked by the Out x Out Gay City Score — the most gay-friendly places for nightlife, safety, community, events, and more, with the top gay bars in each.
$550
Experiences powered by Viator
