The Chicago Bluegrass & Blues Festival was founded in 2008 by Michael Raspatello, Lucas King, Michael Berg, and Leif Moravy (Silver Wrapper) with a bold idea: bring the soul of roots music indoors to heat up Chicago’s coldest months.

“There was nothing offered in the winter months at all… The roots genre was relegated to the summer months,” Raspatello explained in Illinois Entertainer. “As it gets cold out, those styles of music go away—and in my head, there’s no reason why that should happen.” (DNAinfo, 2015)

The festival debuted as a one-day event at the Congress Theater, but quickly found a deep resonance with Chicago audiences. As word spread, CBB evolved into a multi-week, multi-venue celebration of bluegrass, blues, folk, soul, Americana, and all their modern offshoots.

“Blues and bluegrass are the root of everything we have in concert,” Raspatello told Grateful Web. “We feature traditional blues and bluegrass and then go a few branches down the family tree.”

One of the festival’s defining moments took place at the Auditorium Theatre, where legends David Grisman and Del McCoury headlined the “Big Mon Jam”—a tribute to Bill Monroe, the father of bluegrass. Grisman later reflected on the event as:

“A rare opportunity to play to a younger, more varied crowd that’s really listening.” (HuffPost, 2012)

Over the years, CBB became a fixture of Chicago’s independent music scene, presenting more than 200 artists across venues like the Vic, Double Door, House of Blues, Lincoln Hall, Concord Music Hall, Schubas, City Winery, and FitzGerald’s.

Its diverse lineups featured everyone from Jeff Tweedy, Mavis Staples, and Robert Randolph, to then-rising acts like Billy Strings, Greensky Bluegrass, Trampled by Turtles, and The Henhouse Prowlers.

Alongside its musical mission, CBB supported causes like the Saving Tiny Hearts Society, blending purpose with performance.

More than a festival, Chicago Bluegrass & Blues became a seasonal ritual—reminding us that even in the depths of winter, rhythm, roots, and community can light a spark.