Bitter Jester Music Festival Wins 2025 “Best Small Music Festival”

The iconic Bitter Jester Music Festival was just named the "Best Small Music Festival" by the 2025 Festy Awards! Find out why this legendary festival has fans all over the country this summer during the TWENTIETH anniversary Bitter Jester Music Festival. Preliminary concerts will be held at Port Clinton Square (600 Central Ave.) on Friday, June 5, Saturday, June 6, Friday, June 12, and Saturday, June 13. The Grand Finale will take place in Downtown Highland Park on Saturday, June 27. You can also catch special Bitter Jester programming as part of the Taste of Highland Park on Saturday, June 20. Stay tuned for more information about this year’s lineup as well as how you can participate.

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

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.