The 19th annual Pittsfield CityJazz Festival (April 24 – May 4, 2025) kicks off with an open jam session and ends with a jazz brunch at Dottie’s. Events include the popular Jazz Crawl, the jazz prodigy concert, and headline concerts.

On March 29, New York-based sax virtuoso Scott Robinson will be performing 10 numbers by 10 different jazz saxophonists on 10 different saxophones!

Matt and Atla DeChamplain are bringing the Hot Club of New England to the Berkshires on January 5 for a “CD on-ramp” Concert at Proprietor’s Lodge.

Enjoy a a special sneak preview of Natalia Bernal’s upcoming release, En Diablada, on November 30 at the Stationery Factory!

On October 13, alto saxophone lioness and vocalist Grace Kelly brings her quartet and string section to Shakespeare & Co. in Lenox.

October 7–13 Seven days of jazz — a different venue and artist each day! 

The fifth annual Lenox Jazz Stroll takes place in historic Lenox, Massachusetts on September 6–7, 2024.

Check out upcoming Berkshires Jazz events this summer!

Details for the eighteenth annual Pittsfield CityJazz Festival.