You don't want to miss the upcoming 19th Annual Pittsfield CityJazz Festival! From April 24-May 4, 2025! Get ready to immerse yourself in vibrant performances and community events that celebrate the joy of jazz. Music is a universal language that brings families together, and this festival is the perfect opportunity to connect with your loved ones. Enjoy a night of dancing at the Swing Dance, take part in the exciting Jam Session, and explore the city during the Annual Jazz Crawl.
Bring your kids to witness the next generation of talent at the Jazz Prodigy Concert, or treat your family to a delightful Jazz Brunch. With world-renowned headliners gracing the stage, you'll experience the magic of jazz like never before. Come downtown and create lasting memories with your family. Mark your calendars for the Pittsfield CityJazz Festival—where music brings us all closer together!
The Festival at a Glance
- April 24, 7–10pm: Open Jam Session
Dottie’s Coffee Lounge - April 25, 5–11pm: Jazz Crawl — see the Jazz Crawl Schedule below!
Multiple downtown Pittsfield locations - April 26, 7:30–10pm: An Evening with Ben Kohn
Wander Berkshires - April 27, 10am–2pm: Jazz Brunch
Dottie’s Coffee Lounge (music until noon) - April 30, 7pm: Jazz Prodigy Concert
Berkshire Athenaeum - May 2, 7:30pm: Dawning Holmes (purchase tickets)
Barrington Stage Company - May 3, 7:30pm: The Legendary Count Basie Orchestra (purchase tickets)
Colonial Theatre - May 4, 10am–2pm: Jazz Brunch
Dottie’s Coffee Lounge (music until noon)
Starting with an open jam session and ending with a jazz brunch at Dottie's Coffee Lounge, the 19th Annual Pittsfield CityJazz Festival events include the popular Jazz Crawl, the jazz prodigy concert (introducing another young artist to Berkshires audiences), and headline concerts featuring local keyboardist Ben Kohn and his trio, The Legendary Count Basie Orchestra directed by Scotty Barnhart, and vocalist Dawning Holmes with Grammy-winning pianist Jeff Holmes and special guest Avery Sharpe.
There are just two ticketed events — headline concerts featuring the remarkable jazz and blues vocalist Dawning Holmes, and The Legendary Count Basie Orchestra directed by Scotty Barnhart, the last of the touring big bands from the jazz era.
This year’s 10-day festival is supported by lead sponsor Pittsfield Cooperative Bank and generous grants from The Feigenbaum Foundation, the Lewis-Moulin Family Trust, and other donors and sponsors.
Schedule of Events
Please continue to check back for additional details and updates.
Kick-Off Event: Open Jam Session
Thursday, April 24, 7–10pm
Dottie’s Coffee Lounge
The Pittsfield CityJazz Festival kicks-off with an open jam session at Dottie’s Coffee Lounge and restaurant on Thursday, April 24, curated and refereed by pianist Dave Bartley.
Jazz Crawl
Friday, April 25, 5–11pm
Various Downtown Pittsfield Locations
The festival’s annual Jazz Crawl anchors the opening weekend events, and features local artists in restaurants and lounges throughout Pittsfield:
- 5–7pm: Paul Ostermayer Trio
Hot Plate Brewing Co.
1 School St. - 6–8:30: Andy Kelly Trio
101 Restaurant & Bar
1 West St. (Holiday Inn) - 6–9pm: Ben Kohn Trio
Dottie's Coffee Lounge
444 North St. - 7–10pm: Michael Junkins Trio
Methuselah Bar & Lounge
391 North St. - 8:45–10:15pm: Jason Ennis Trio
Hotel on North
297 North St. - 9–11pm: Lucky 4 quartet, dance set
WANDER Berkshires
34 Depot St., Alley
Jazz Prodigy Concert
Wednesday, April 30, 7pm
Berkshire Athenaeum
The Jazz Prodigy Concert kicks-off “headline week” on Wednesday, April 30 at the Berkshire Athenaeum. Introducing another young artist to Berkshires audiences, the concert takes place on International Jazz Day, a global celebration that is organized by UNESCO. The concert, sponsored by The Friends of the Athenaeum, presents bassist Esteban Ruiz, a discovery from the Litchfield Jazz Camp, backed by Ben Kohn on piano and Conor Meehan on drums.
Headline Concerts
An Evening with Ben Kohn
Saturday, April 26, 2025 at 7:30pm
Wander Berkshires (34 Depot St., Pittsfield)
FREE!
The preeminent keyboard artist in the region, Kohn will appear with his trio and special guests in a cabaret setting at Wander Berkshires (soft drinks available; BYOB; access will be available to Tito’s Mexican Bar & Grill).
Dawning Holmes
Friday, May 2, 2025 at 7:30pm
Barrington Stage Company, Pittsfield
Headline weekend for the Pittsfield CityJazz Festival kicks off with the remarkable vocalist Dawning Holmes, appearing with Grammy winner Jeff Holmes on piano and trumpet, and special guest Avery Sharpe on bass.
The Legendary Count Basie Orchestra directed by Scotty Barnhart
Saturday, May 3, 2025 at 7:30pm
Colonial Theatre, Pittsfield
Experience the timeless swing of The Legendary Count Basie Orchestra as they headline the Pittsfield CityJazz Festival at The Colonial Theatre. Under the masterful direction of Scotty Barnhart, this legendary ensemble continues to set the gold standard in jazz, recently earning their 18th Grammy Award for Basie Swings The Blues in 2024. With a rich history of captivating performances for audiences worldwide, the Count Basie Orchestra’s upcoming concert promises an evening of unparalleled musical excellence. Denise Thimes will be guest vocalist with the Basie ensemble.
Adding to the night’s excitement, the Berkshires Jazz All Star Youth Ensemble will open the show, showcasing the region’s emerging talent. Don’t miss this unique opportunity to witness both the future and the legacy of jazz in one unforgettable evening.
