Twentieth Annual Pittsfield CityJazz Festival

A Profile of Women in Jazz

April 17–25, 2026

Downtown Pittsfield, MA

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The twentieth annual Pittsfield CityJazz Festival (April 17–25) is a profile of Women In Jazz. The headline concerts feature:

Georgia Heers, a rising artist who channeled Ella Fitzgerald in George Clooney’s 2025 Broadway reincarnation of “Good Night and Good Luck.”

Grace Kelly, a titan of the alto saxophone, who has just completed her twentieth year as a professional performer.

Veronica Swift, perhaps the most successful crossover vocalist on the jazz/rock scene today.

Ticketed Headline Concerts

Ticketed concerts will take place on the campus of Barrington Stage:

• April 18: Georgia Heers sings the music of Billie Holiday in the intimate (and most Billie-like) setting of Mr. Finn’s Cabaret

• April 25: The capstone concert, with Grace Kelly, Veronica Swift, and the UConn Jazz Ensemble, will be at the Boyd-Quinson Stage, the site of the first Pittsfield CityJazz Festival in 2005.

Jazz Crawl & More

Interspersed among the 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..

• April 17: Jazz Crawl (restaurants and lounges throughout Pittsfield’s Upstreet Cultural District)

• April 22: Jazz Prodigy concert (Berkshire Athenaeum)

• April 24: Jam Session (venue TBA)

Details will be announced to the media and on our website when ticket prices are finalized.