Trophy Room

10/13/2026

We've been brewing up something good. 🔮🍸

Our new fall cocktail menu has officially arrived, and we're leaning into spooky season with some wickedly good sips. 👻🍂

From pumpkin spice espresso martinis to apple c***r margaritas and smoky old fashioneds, we've got a little something to get you in the spirit.

Come sip your way through fall at Trophy Room! 🥃✨

09/30/2026

No tricks. Just queens and treats. 👻🍸

Halloween Spooktacular Drag Brunch is taking over Trophy Room with and

https://www.facebook.com/share/18iTqGw6kF/

Sunday, Oct. 25 | 2–4 PM | FREE

09/30/2026

A little something for every kind of October. 👻🏈🏒🍸

Game days, Drag Brunch, and one very spooky Halloween at Trophy Room.

Save the calendar and we’ll see you soon!

09/28/2026

Trophy Room of Horrors is taking over Halloween night. 🕸️🕯️

Join us Saturday, October 31 for spooky drinks, witchy vibes and a costume contest with prizes for the best looks of the night.

https://www.facebook.com/share/1DvCNudeci/

8 PM–1 AM

📍 Trophy Room | 26 Chandler St.
🎃 Costume contest, drinks & MORE

Trophy Room is located at the corner of Berkeley and Chandler in Staypineapple, A Delightful Hotel, in the historic South End neighborhood.

09/15/2026

We’ve carefully reviewed all possible outcomes. You should probably get a drink. 🍸

09/11/2026

Every friend group has one of these: A Lychee Martini, an Espresso Martini and a Trophy Wife

You can't convince us otherwise! 💁

09/10/2026

Meet Naun! 👋🍍

From prepping food and serving guests to training behind the bar, Naun does a little bit of everything at Trophy Room.

His favorites? Making pupusas and tacos, sipping a b**r or margarita and getting out on the soccer field whenever he can. ⚽🌮🍹

Next time you’re in, be sure to say hi to Naun!

09/09/2026

Dolly deserves a celebration, and we’re giving her one. 💖🤠✨

Join Shady Gaga and Adrianna Drag for a Dolly Parton Drag Brunch packed with big hair, big songs, big performances and plenty of rhinestones.

Sunday, September 27
2–4 PM
FREE
Trophy Room, 26 Chandler St.

Come celebrate an icon with us. 💕

https://www.facebook.com/share/1FWnDzRSfe/

09/04/2026

Just one? It’s a long weekend. Be serious. 🍹

Kick off Labor Day weekend at Trophy Room with a cocktail (or two… or three), good food and absolutely no reason to rush home.

We’ll be here all weekend, so come see us at 26 Chandler. 🍍

09/02/2026

Trophy Room won’t be quite the same without this guy. 🥹🍸

Our bartender Isaac is trading Boston for San Francisco, and his last day behind the bar is Sunday, September 6!

Come by before he heads west to grab a drink, give him a hard time one last time and help us send him off properly. 💚