Entertainment & Experiences in Boston, MA
25 places · 4 free · 23 indoor · Updated 2026-10-19
Huntington
Acoustics designed by actual scientists in 1900
500,000 works, pay-what-you-wish third Thursdays
Empty frames from the 1990 heist still hang
Theater District
Chappelle and Mulaney have both played here
Seinfeld, Leary, and Steven Wright played here
1925 movie palace with the original gilt interior
North End
College students get in for $20 day-of
In-house winery, dinner at your table during the show
Seaport
Free every Thursday 5-9pm, under 18 always free
300-seat club, national headliners, $20-45
LED swings that glow and change color, free
Fenway
5,000 capacity, right next to Fenway Park
Comedy for $10-20 at an Irish pub by Fenway
Sunday gospel brunch is the sleeper hit
Cheapest comedy in Boston, $5-15
Bowling near Fenway, $7-12 a game
Allston
U2, The Police, and Radiohead all played here early
200-seat room, serious jazz and world music
3,500 capacity, no bad sightline anywhere
South End
No cover, live jazz every single night since 1947
Live music every night, no cover, food is real
Cambridge
4,300 glass flowers from the 1890s that look real
Restaurant-quality food at a 525-seat music venue
Single-screen indie cinema since 1953
Back Bay
Free concerts on the Charles River all summer