The Pittsfield CityJazz Festival was formed in 2005 to present mainstream and traditional jazz in a downtown setting. Over its first four years, the festival has presented such headline talent as NEA Jazz Masters Billy Taylor and Phil Woods; up-and-coming artists such as Grace Kelly; individual standouts such as TS Monk, Jr., Claire Daly, Peggy Stern, Winard Harper and Barbara Dennerlein. The New England Jazz Ensemble released a ‘live’ recording of that band’s appearance at the festival. The festival’s 2005 opening act, The New Black Eagle Jazz Band, was the first group to make a return engagement, appearing with the Pittsfield CityJazz Youth Orchestra in 2008.
An annual highlight has been Jazz In Schools, featuring performances, demonstrations, and discussions by the Pittsfield Sister City Jazz Ambassadors in the schools of Pittsfield. Over the years, literally thousands of students have experienced live jazz in the classroom and assembly halls. This local group, which has toured Pittsfield’s sister cities abroad, is headed by guitarist and teacher Andy Kelly. School principals and administrators have praised this community commitment of the festival and the positive impact it has had on students. Thanks to generous underwriters, Jazz In Schools is provided at no cost to the school system.
The festival also presents Jazz About Town, featuring local musicians in restaurants across the city. Dozens of venues have featured all genres of instrumental and vocal jazz, all at no cover, in advance of weekend headline concerts. Restaurant owners report increased attendance and longer visits by patrons on the nights when they have participated in this aspect.
In an effort to keep prices at an accessible level, the Pittsfield CityJazz Festival has successfully partnered with several local, regional, and national organizations to underwrite various components. Starting with Legacy Banks in 2005, sponsors have included Greylock Marketing Group, TD Banknorth, The Red Lion Inn, Time Warner Cable, the Crowne Plaza Hotel, MTV/Nickelodeon, the National Endowment for the Arts, and the Pittsfield Cultural Council. Local merchants have provided thousands of dollars in in-kind services such as Lenox Softworks, ReadWebCo, The Berkshire Eagle, Aldam Press and Wood Brothers.