Interspersed among the 2026 Pittsfield CityJazz headline concerts will be the annual “jazz crawl,” a jam session, and our jazz prodigy concert, the latter sponsored by the Friends of the Athenaeum.

Times and various locations in Downtown Pittsfield.

6-8PM: Jack DiNicola Trio
Tito's, 34 Depot St.

6-8PM: Michael Junkins Trio
Methuselah, 391 North St.

6:30-8:30PM: The Jolly Ranchers
Rare 297 (Hotel on North), 297 North St.

7-9PM: Andy Wrba Trio
BB's at the Lantern, 455 North St.

8-10PM: Dance set with The Lucky 5
WANDER Berkshire, 34 Depot St.