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Bitter Jester Music Fest

Bitter Jester Music Festival 

BJMF Circle Logo Purple_Transparent_Lot-2023

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..."

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.

A series of preliminary concerts will be held at Port Clinton Square* starting at 6 PM on June 7, 8, 14, and 15.  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 at  The Lot** on Saturday, June 29 from 2 - 10 PM. The winning band will be announced at the end of the night and a $2,0000 cash prize will be given!

Applications for bands and solo artists are accepted by Bitter Jester on their website (typically early February through late April). At least half of the participants must be 21 years of age or younger in order to apply but other performance opportunities exist through Bitter Jester. Learn more at

Bitter Jester Music Festival 2023_Preliminary Concert_Port Clinton_01_PHOTO by Alex Glassman - Copy - Copy - Copy

About the Bitter Jester Music Festival

This summer-long music competition and concert series is produced by the Bitter Jester Foundation for the Arts, NFP, a 501(c)(3) not-for-profit charitable organization based in Highland Park.

With an unparalleled amount of educational feedback provided to participants plus opportunities to perform additional Bitter Jester Showcase Concerts at both Ravinia Festival in Highland Park and Navy Pier in Chicago, this festival isn't just fun for audiences, it's great for musicians, too! Follow BJMF on their Instagram @bitterjester_musicfestival or email for more information or to apply.

The City of Highland Park has been a proud sponsor of this non-profit free concert series since its inception.


*Port Clinton Square is located at 600 Central Ave. in downtown Highland Park.

**The Lot is located at the intersection of St Johns and Central Avenues in Highland Park.