The 20th Annual Pittsfield CityJazz Festival in MA | April 17th-25th, 2026
Grace Kelly, Veronica Swift, and Georgia Heers
to Perform at Twentieth Annual
Pittsfield City Jazz Festival, April 17-25
Lineup Features Headliners,
Rising Artists, Local Musicians,
Jam Session, a Jazz Prodigy,
and a New Eponymous Beer
PITTSFIELD, Mass., March 16, 2026 – Berkshires Jazz, Inc. today announced the lineup for the twentieth annual Pittsfield CityJazz Festival, which runs from April 17-25 in venues throughout the City’s Upstreet Cultural District. Presenting the gamut of artists, from prodigies and local musicians to rising stars and top names, headline concerts feature Grace Kelly, Veronica Swift, and Georgia Heers. Most of the events are free, including an open jam session, the annual jazz crawl, and a jazz prodigy concert.
The festival is made possible by a $15,000 grant from The Feigenbaum Foundation, sponsorship by the Greylock Federal Credit Union, and private donations.
The two headline weekends represent a veritable profile of women in jazz, with Georgia Heers’ tribute to Billie Holiday already sold out, and the capstone concert featuring two of the jazz world’s powerhouses. Saxophonist, composer, and singer Grace Kelly, and jazz/rock crossover vocalist Veronica Swift, will appear together for the first time, and will be backed by the University of Connecticut Jazz Ensemble.
The festival kicks-off with a jam session on April 17, at Hot Plate Brewing Co., 1 School Street, Pittsfield. Pianist and leader Dave Bartley hosts the open jam session, with local musicians invited to bring their own instruments and sit it. Berkshires Jazz has learned that Hot Plate will be introducing a special brew to honor the occasion.
Georgia Heers’ cabaret show, on April 18, sold out within 24 hours after it was announced to Berkshires Jazz followers. Heers played Ella Fitzgerald in George Clooney’s Broadway recreation of “Good Night and Good Luck,” and wowed the audience when she appeared with Emmet Cohen last October at Tanglewood. She is returning to perform a one-night-only tribute to Billie Holiday, in Mr. Finn’s Cabaret & Bar.
The music resumes on Wednesday, April 22, with the annual Jazz Prodigy concert at the Berkshire Athenaeum. Sponsored by the Friends of the Athenaeum, this year’s concert introduces 14-year-old drum phenom Xander Rosenblum, who will be playing with a local all-star group headed by pianist George Oldziey, and including Paul Ostermayer on saxophone and Adam Cote on bass.
Friday, April 24 is the Jazz Crawl, when several restaurants and lounges will be hosting jazz performances. Spread throughout Pittsfield’s North Street business and hospitality corridor, the jazz crawl runs from 5-10 p.m. The full schedule will be published as the slots get filled out.
Two of the most popular artists ever to appear in the Berkshires cap the festival’s final weekend. Veronica Swift and Grace Kelly have been making music professionally for twenty years, and have been on parallel paths on the global concert, club, and festival scene. Kelly first appeared at the Pittsfield festival as a 14-year-old guest of Phil Woods, returning five years later as the headliner with Woods as her guest. Swift first appeared in the Berkshires at the 2018 festival with a local all-star trio. She impressed the crowd so much that she returned to the main stage in a double billing with her mother, Stephanie Nakasian, in 2019.
Swift and Kelly will be backed by the University of Connecticut Jazz Ensemble, under the direction of John Mastroianni. The UConn big band is considered one of the top collegiate jazz ensembles in the nation. The capstone concert takes place at the Boyd-Quinson Stage, on the campus of Barrington Stage Co. It is same stage as the inaugural Pittsfield CityJazz Festival in 2005, when the building was known as the Berkshire Music Hall.
Updates and further details will be posted regularly at www.BerkshiresJazz.org.
Tickets for the capstone concert are available at Barrington Stage.
Berkshires Jazz, Inc. is a 501c3 non-profit organization whose mission is to preserve jazz, America’s indigenous music, and nurture its grown by presenting high-quality programs, fostering jazz education, and promoting the local jazz scene. The organization was formed from the all-volunteer committee that had been planning the Pittsfield CityJazz Festival, which launched in 2005.
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