Twentieth Annual Pittsfield CityJazz Festival

A Profile of Women in Jazz

April 17–25, 2026

Downtown Pittsfield, MA

• Friday, April 17 at 7pm: Jazz Jam (Hot Plate Brewing, Pittsfield)

• Saturday, April 18 at 7:30pm: Georgia Heers (Barrington Stage/Mr. Finn’s Cabaret, Pittsfield)

• Wednesday, April 22 at 7pm: Jazz Prodigy concert (Berkshire Athenaeum, Pittsfield)

• Friday, April 24: Jazz Crawl (restaurants and lounges throughout Pittsfield’s Upstreet Cultural District — see venues below)

• Saturday, April 25 at 7pm: Grace Kelly & Veronica Swift (Barrington Stage, Pittsfield)

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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 at 7:30pm: Georgia Heers — SOLD OUT!

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

April 25 at 7pm: Capstone Concert

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.

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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.

• Friday, April 17 from 7–10pm: Jazz Jam (Hot Plate Brewing, Pittsfield)

• Wednesday, April 22 at 7pm: Jazz Prodigy concert (Berkshire Athenaeum, Pittsfield)

• Friday, April 24 from 6-10pm: Jazz Crawl (restaurants and lounges throughout Pittsfield’s Upstreet Cultural District)

  • 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
    Dottie’s, 444 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.

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