Hotels for Dermot Kennedy: The Weight of the Woods Tour

Outdoor summer-into-autumn shows at a ballpark carry a different energy than an arena tour, with the crowd spread across the field and stands rather than packed into a pit. Kennedy's songwriting leans on big, aching choruses built for exactly this kind of open-air singalong, where thousands of voices carry further than they would indoors.

An early Friday start suggests a long evening ahead, with support acts likely filling the hours before the headline set as the sky darkens overhead. Expect a night shaped as much by the setting as the setlist, folding baseball history into a gig.

The oldest ballpark in Major League Baseball, Fenway Park is a beloved Boston institution, home to the Red Sox and its famous 'Green Monster' wall, and a characterful host of summer concerts. The surrounding Kenmore and Fenway area buzzes with students, bars and restaurants, with the rest of compact Boston easily walkable.

The MBTA Green Line stops right by the park. Booking a room in Boston lets you soak up the pre-game atmosphere on foot and ride the T back with ease afterwards.