Unique Things to Do in Boston
Boston's most unique experiences include The Mendoza Line speakeasy-style bar, Improv Asylum comedy in a converted North End basement, Lansdowne Pub pre-game atmosphere steps from Fenway, and the House of Blues in a restored 1920s Fenway building.
4 places · 1 free · Updated Oct 2026
The oldest public park in America offers year-round family fun. In summer, the Frog Pond spray pool is free for kids 12 and under (opens late June). In winter, outdoor ice skating takes over. The Tadpole Playground near Frog Pond has whimsical frog-themed climbing structures. A historic carousel operates seasonally.
Amphibious WWII-style vehicles tour Boston's historic landmarks on land before splashing into the Charles River. Departures from Museum of Science, Prudential Center, and New England Aquarium. Tours run rain or shine every 30 minutes from 9am to about an hour before sunset, April through late November.
Historic 1,200-seat theater in the Theater District hosting stand-up comedy, live music, and special events. Built in 1914, the intimate venue has hosted everyone from Dave Chappelle to John Mulaney. Ticket prices vary widely by performer -- expect $30-80 for most comedy shows, with bigger names commanding $60-150+.
Comedy night series at The Dugout Cafe near BU featuring stand-up, roasts, and open mic nights. A more underground, casual comedy experience compared to the polished clubs. Cover is usually $5-15, making it one of the cheapest comedy options in the city. Popular with the BU and college crowd. Check their social media for the weekly lineup.