Bitter jester music festival: SEASON TWENTY!!
Discover your next favorite band at Bitter Jester.
Celebrating TWENTY YEARS, The Bitter Jester Music Festival (BJMF) is the nation’s oldest and largest professional multi-state music competition for emerging bands and solo artists. Attracting entries from nearly half the country, BJMF supports and promotes young and up-and-coming talent from across the Midwest and beyond.
We are a non-profit committed to providing FREE, family-friendly, summer-long concerts that are open to the public. With no restrictions on music genres for artists that apply, BJMF introduces audiences young and old to something new, something fresh, and something fun.
You’ll be sure to discover your next favorite band at Bitter Jester!
Plan your trip by checking out the 360 tour of Port Clinton (plus surrounding parking, shopping, and dining via the menu squares):
Follow us on Instagram and Facebook for the latest info and updates.
Click here to learn about the performers featured during the our previous season. And click the records below to learn more about our very first DOUBLE LP on vinyl, “Live at Bitter Jester Music Festival, vol. 01” recorded at Billy Corgan’s (Smashing Pumpkins) Madame Zuzu’s Tea House!and. The second volume, produced last year, was recorded at various venues in Highland Park and at Navy Pier in Chicago! Get your copy of Volume One here and Volume Two can be purchased here! Or come by and pick one up at any of our 2026 concerts! You can also purchase Volume Three here!
Congratulations to our 2025 Music Fest Winners:
Platinum Moon (Grand Champions), Charlieboy (Runners-Up), and Exit 122 (Honorable Mention)!
Meera Raphael, Anton Klettner, Toby Dorfman, and Owen Jackson won Vocalist, Guitarist, Bassist, and Drummer of the Year Awards (respectively) with Adri Friebel winning the 2025 “Michael Brook Outstanding Instrumentalist Award” for Bassoonist of the Year! Alexander Sherk took home a special drumming prize awarded by Ludwig Artist Jessica Burdeaux.
Listen to a mashup of commentary from our past musicians!
Since 2020 our Grand Prize Money has been generously donated by First Bank of Highland Park, a Title Sponsor for our Grand Finale Concert!
Proud to be celebrating 20+ summers of quality musical performances and educational feedback for up-and-coming bands and solo artists!
The Bitter Jester Music Festival is a competition and concert series built on a strong foundation of community and emboldening and empowering young performers at a critical time in their social and artistic development. BJMF gives participating young adults an opportunity to receive professional feedback from working musicians and, most importantly, meet and connect with dozens of other musicians their own age. Additionally, performers get to work hand-in-hand with Bitter Jester Studio’s nine-time Emmy award winning production team, providing them with a level of media exposure, professional mentorship, and networking that is unmatched by other similar competitions.
The event has four preliminary competitions on consecutive weekends in June at Port Clinton Square in downtown Highland Park, IL. A winner is selected by qualified judges each night to compete in the Grand Finale Concert. After all four preliminary competitions, Bitter Jester Producers decide on four "Wild Cards" - bands/solo artists who will also compete for the title at a big Grand Finale concert. Showcase bands are also selected to perform on the Bitter Jester Mobile Stage prior to the Grand Finale battle. -- An annual "Best Of" takes places each Labor Day at the Beer Garden on Navy Pier.
The Bitter Jester Music Festival is made possible, in part, by tremendous support from the City of Highland Park, IL, support from First Bank of Highland Park, and a grant from the Highland Park Community Foundation. Click here to read what Mayor Rotering has to say about the festival.
“It has become a summer tradition to attend Bitter Jester concerts...”
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2026 Bitter Jester Music Festival Dates & Competition Timeline:
JAN. 15, 2026: Applications Go Live!!
MAR. 1, 2026: Early Application Deadline
APRIL 15, 2026: Application Deadline
MAY 1-3, 2026: All Entrants Notified
MAY 8, 2026: Official Lineup Announced
JUNE 5, 2026: Opening Night Preliminary Concert
JUNE 6, 2026: Night Two Preliminary Concert
JUNE 8, 2026: Satellite Concert #1 @ Chicago Botanic Gardens
JUNE 12, 2026: Night Three Preliminary Concert
JUNE 13, 2026: Night Four Preliminary Concert
JUNE 15, 2026: Satellite Concert #2 @ Chicago Botanic Gardens
TBA, JUNE 2026: Wild Cards Announced!!
JUNE 27, 2026: Grand Finale Concert
TBA, SUMMER, 2026: A Bitter Jester Band Opens @ Ravinia Festival
SEPT. 7, 2026: “Best Of” Showcase @ Navy Pier
The Bitter Jester Music Festival is supported, in part, by financial contributions from the City of Highland Park, First Bank of Highland Park, Judy’s Pizza, the Highland Park Community Foundation, Elmore Pedals, and many individual donors just like you.
The Festival has exciting ongoing partnerships with Ravinia Festival, Navy Pier, and the Chicago Botanic Garden to showcase exceptional musicians each year. Past partnerships include The Chicago/Midwest Emmy Awards and Harry Caray’s Restaurant Group.
Ravinia hosts one Finalist band as an opening act before a national headliner on their beautiful Carousel Stage. Navy Pier hosts a day-long “Best Of” showcase concert on Labor Day each year to close out their “Live on the Lake” summer series.
This Bitter Jester Foundation for the Arts and its Music Festival are partially supported by a grant from the Illinois Arts Council through federal funds provided by the National Endowment for the Arts.
Some of our supporters (donating gift cards and other in-kind contributions) over the years have included:
