20th Anniversary
Bitter Jester Music Festival Preliminary Concert - Night Two
JUN. 6 | 5 PM - 10 PM | FREE
Port Clinton Square | 600 Central Ave.
Discover your next favorite band at Bitter Jester! This free, family-friendly concert series has been taking place in Downtown Highland Park since 2006! What started as a small "battle of the bands" for local performers has evolved into the Midwest's largest showcase for emerging artists. With performers coming from nearly a dozen states and vying for $3,500 in cash prizes, the Bitter Jester Music Fest is a must-see event!
As 101.9 The Mix put it: "Come out and say hi! It's going to be an incredible concert with a bunch of future headliners!" So check out some of your next favorite bands and be able to say "I saw them when..."
Multiple high-quality acts perform each night and receive detailed feedback from industry professionals. A winner is selected at each of the four Preliminary Concerts and four "Wild Cards" are chosen at the end of the summer by Festival Producers. Those eight acts then compete at a Grand Finale Concert.
Select Bitter Jester Finalists are chosen to open for national headliners on Ravinia's Carousel Stage and also perform a "Best Of" show at Navy Pier's Beer Garden on Labor Day each year.
Stay tuned for additional details regarding the 2026 Bitter Jester Music Festival.