Stylized text reading 'Chicago Bluegrass, Classics and Blues' in a vintage font with shadow effects on a black background.

Since 2008, this wintertime celebration of roots music and its offshoots brought legends and rising stars to Chicago stages — from The Avett Brothers, String Cheese Incident and Jeff Tweedy to Béla Fleck, Grace Potter, and David Grisman.

With over 300 artists across bluegrass, blues, folk, and Americana, the festival became a soulful gathering of sound, community, and discovery.

Acoustics Anonymous • Alex Wilson • American Babies • Bailiff • Ben Ripani Music Co. • Béla Fleck & the Flecktones • Billy Strings • Blackdog • Blue Mother Tupelo • Blue Room Hero • Cobalt & The Hired Guns • Clusterpluck • Colter Wall • Congress of Starlings • Cornmeal • Cory Chisel & The Wandering Sons • Curtis Harding • Daphne Willis • Dawes • David Grisman • David “Honeyboy” Edwards • Del McCoury Band • Derek Nelson & The Musicians • Donna the Buffalo • Donnie Biggins • Dr. Dog • Drive-By Truckers • Drew Holcomb & The Neighbors • Eddy “The Chief” Clearwater • Edward Sharpe & The Magnetic Zeros • Emmitt-Nershi Band • Environmental Encroachment • Escondido • Evergreen Grass Band • Frank Vignola & Vinny Raniolo • Grace Potter & The Nocturnals • Great Divide • Greensky Bluegrass • Ha Ha Tonka • Head for the Hills • Henhouse Prowlers • Holy Ghost Tent Revival • Horseshoes & Hand Grenades • Huckleberry Green • Jaik Willis • Jamie Lono • Jeff Austin Band • Jeff Tweedy • Jennifer Hartswick Band • Jessica Lee • Joe Pug • Joe Purdy • Jon Batiste • Jon Drake & The Shakes • Jonas Friddle • Justin Townes Earle • Leo Kottke • Leagues • Liberty Bluegrass Band • Lil’ Ed & The Blues Imperials • Lindsey O’Brien & Friends • Lucero • Majors Junction • Marc Broussard • Mary Lane & The No Static Blues Band • Matador! Soul Sounds • Mike Mangione & The Union • Miss Jackie & The Sass • New Orleans Suspects • Nick & The Ovorols • Nick Cassarino & The Sisters Of Salvation • Otis Clay • Paleface • Paper Thick Walls • Pert Near Sandstone • Rayland Baxter • Robert Randolph & The Family Band • Ronnie Baker Brooks • Rusted Root • Sexfist • Shemekia Copeland • Steve Earle • Swear and Shake • Tangleweed • Terrance Simien & The Zydeco Experience • The Autumn Defense • The Avett Brothers • The Devil Makes Three • The Felice Brothers • The Frizz • The Giving Tree Band • The Howlin’ Brothers • The New Old Calvary • The O’My’s • The Right Now • The Sadies • The Shams Band • The Skatalites • The String Cheese Incident • The Travelin’ McCourys • The Traveling Suitcase • Tiny Miles & The Big Kids • Todd Kessler & The New Folk • Trampled By Turtles • Uncle Zesty’s Oldtime Bootknockers • Van Ghost • Will Jacobs

Acoustics Anonymous • Alex Wilson • American Babies • Bailiff • Ben Ripani Music Co. • Béla Fleck & the Flecktones • Billy Strings • Blackdog • Blue Mother Tupelo • Blue Room Hero • Cobalt & The Hired Guns • Clusterpluck • Colter Wall • Congress of Starlings • Cornmeal • Cory Chisel & The Wandering Sons • Curtis Harding • Daphne Willis • Dawes • David Grisman • David “Honeyboy” Edwards • Del McCoury Band • Derek Nelson & The Musicians • Donna the Buffalo • Donnie Biggins • Dr. Dog • Drive-By Truckers • Drew Holcomb & The Neighbors • Eddy “The Chief” Clearwater • Edward Sharpe & The Magnetic Zeros • Emmitt-Nershi Band • Environmental Encroachment • Escondido • Evergreen Grass Band • Frank Vignola & Vinny Raniolo • Grace Potter & The Nocturnals • Great Divide • Greensky Bluegrass • Ha Ha Tonka • Head for the Hills • Henhouse Prowlers • Holy Ghost Tent Revival • Horseshoes & Hand Grenades • Huckleberry Green • Jaik Willis • Jamie Lono • Jeff Austin Band • Jeff Tweedy • Jennifer Hartswick Band • Jessica Lee • Joe Pug • Joe Purdy • Jon Batiste • Jon Drake & The Shakes • Jonas Friddle • Justin Townes Earle • Leo Kottke • Leagues • Liberty Bluegrass Band • Lil’ Ed & The Blues Imperials • Lindsey O’Brien & Friends • Lucero • Majors Junction • Marc Broussard • Mary Lane & The No Static Blues Band • Matador! Soul Sounds • Mike Mangione & The Union • Miss Jackie & The Sass • New Orleans Suspects • Nick & The Ovorols • Nick Cassarino & The Sisters Of Salvation • Otis Clay • Paleface • Paper Thick Walls • Pert Near Sandstone • Rayland Baxter • Robert Randolph & The Family Band • Ronnie Baker Brooks • Rusted Root • Sexfist • Shemekia Copeland • Steve Earle • Swear and Shake • Tangleweed • Terrance Simien & The Zydeco Experience • The Autumn Defense • The Avett Brothers • The Devil Makes Three • The Felice Brothers • The Frizz • The Giving Tree Band • The Howlin’ Brothers • The New Old Calvary • The O’My’s • The Right Now • The Sadies • The Shams Band • The Skatalites • The String Cheese Incident • The Travelin’ McCourys • The Traveling Suitcase • Tiny Miles & The Big Kids • Todd Kessler & The New Folk • Trampled By Turtles • Uncle Zesty’s Oldtime Bootknockers • Van Ghost • Will Jacobs

Musicians performing on stage, one playing a banjo and another playing an acoustic guitar, both singing into microphones.

Aragon Ballroom • Auditorium Theatre • Chop Shop • City Winery Chicago • Concord Music Hall • Congress Theater • Double Door • Fitzgerald’s (Berwyn) • House of Blues Chicago • Lincoln Hall • Martyrs’ • The Metro • Old Town School of Folk Music • Park West • Schubas Tavern • Subterranean • SPACE (Evanston) • Thalia Hall • Tonic Room • The Riviera Theatre

Poster advertising a music festival featuring bluegrass and blues bands, scheduled for Saturday, November 22, 2008, at the Congress Theater in Chicago, with tickets costing $31, supporting the Saving Tiny Hearts Society.
Event poster for Chicago Bluegrass and Blues Festival on December 12, 2009, at the Congress Theater in Chicago, Illinois. Features performances by Béla Fleck & the Flecktones, Dr. Dog, Emmitt-Nershi Band, Eddy 'The Chief' Clearwater, and others. Incl
A promotional poster for the Chicago Bluegrass and Blues Festival featuring illustrated musicians, including a man with a beard and a woman with wild hair, holding a cigarette. The poster lists the festival dates from December 3 to December 5, with v
Poster for the 4th annual Chicago Bluegrass and Blues Festival featuring drive-by truckers, DAWS, Joe Pug, Bailife, Van Ghost, Jaik Willis, Great Divide, Jon Drake & The Shakes, Ben Ripani Music Co., Go Long Mule, band called Catch, Paper Thick Walls
Poster for the 5th Annual Chicago Bluegrass and Blues Festival listing performances from various bands and artists, scheduled at Concord Music Hall in Chicago from January 10 to February 1, 2014, with tickets available at clubtix.com.
Concert poster for the Chicago Bluegrass and Blues Festival, February 9th to 21st, listing performers, venues, and ticket information.
Festival poster for Chicago Blues, Grass, and Blues music event held from March 21 to 25, 2018, listing performers such as Curtis Harding, Colter Wall, Horseshoes & Hand Grenades, and others, with a background illustration of a large tree and forest
A digital illustration of an outdoor concert scene at sunset with a big billboard announcing Jeff Tweedy's live performance at the drive-in theater, featuring a crescent moon, two trees, a fire, a vintage truck, and small animals.
Vintage style poster for a music event titled 'At the Drive Inn,' featuring the band 'Trampled by Turtles,' with concert dates Saturday, September 19, and Sunday, September 20, 2020, in McHenry, Illinois. The poster includes decorative stars, an arro
Promotional poster for the 'On the Drive Inn' live music concert series featuring blues and blues, with a cosmic background, rows of cars, and a large colorful circular graphic with three silhouetted musicians on stage.