Bitter Jester Music Festival

Bitter Jester Music Festival Annual nonprofit FREE music festival and concert series - Discover Your Next Favorite Band at Bitter Jester! More info: bitterjestermusic.org

Established in 2006 as a partnership between the City of Highland Park and the Bitter Jester Foundation for the Arts (a 501(c)(3) non-profit), the annual Bitter Jester Music Festival has been growing steadily since its inception. The festival features a Battle of the Bands style competition and multiple opportunities for bands and solo artists to showcase their talent. All bands with a majority of

members who are under the age of 21 are eligible to apply, including junior high and college bands! Cash and other prizes (often including concert tickets, studio time, gear, photo shoots, gift certificates, and more) is provided by numerous generous sponsors. Cash prizes are provided by First Bank of Highland Park. The main part of the festival takes place in three rounds:

ROUND I: FRIDAY NIGHT PRELIMINARY CONCERTS
These typically take place on Friday nights in June (check website for up to date info). Six (6) bands compete each Friday and are judged - showcase musicians are also featured. A professional sound crew is at the disposal of the bands all night long and the concert audio is recorded. The winning band from each Friday advances to the Finals on the 4th of July. There is a non-refundable application fee to enter. Not all bands are accepted. Solo performers welcome. All concerts are FREE and open to the public! ROUND II: FINALS
The Finals take place on a professional sound stage on the 4th of July (check website for up to date info) as the concert leading up to the City of Highland Park's Fireworks display. All bands will have a professional sound-check prior to the concert. The winners of the Friday Night Concerts duke it out in the semi-finals and are judged by professional musicians. Judges narrow the Finalists down to two (2) winning bands, who proceed to Round III, the final round. This event is FREE and open to the public! FOOD WILL BE AVAILABLE and families are encouraged to stay for the fireworks. ROUND III: FINAL PLAYOFF
Also held on the 4th of July on the same stage, the final two (2) bands then each play a single song. The audience cheers and applauds back and forth for the their favorite as the judges cast one final vote and Grand Champion is announced. The bands are awarded their prizes at the close of the night as the City's fireworks display goes off.

06/14/2026

We had such wonderful audiences at our first weekend of the 20th anniversary of Bitter Jester! Thank YOU for supporting ...
06/11/2026

We had such wonderful audiences at our first weekend of the 20th anniversary of Bitter Jester! Thank YOU for supporting live music and upcoming artists. We still have even more talent that you and your family can enjoy this weekend at Port Clinton Square. Our lineup will have you grooving and moving your feet, we can’t wait to see you on 6/12 & 6/13!

06/10/2026

SOUND ON! Sneak peak of Bitter Jester Music Fest Night 4: June 13 @ 5:30pm! Discover your next favorite band this summer in

🎸In Competition on Night Four:

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🎙️Featured Showcases on Night Four:


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🎤Guest Artists on Night Four:




44 bands & soloists from two dozen states descend upon Chicagoland for Bitter Jester this season. So come on out and kick back with a cool drink or grab a bite to eat as you find some incredible new artists to add to your Spotify when you leave the festival.

Night Four Judges (all BJMF alumni!) are:

•Maggie Fewles (2018 Finale Showcase Performer)
•Kate Larson (2021 & 2022 Guest Artist)
•Daniel Jonak (2014 & 2016 Grand Champion)
•Jonah Brooks (2012 Grand Champion)
•Ben DeWitt (2020 Grand Champion)

… with Glenn Williams (retired Music Educator & Nic DeGrazia’s HS Band Director!) & Michael Tseitlin (three-time Honorable Mention winner) providing verbal commentary for the bands!

Huge thank you to our sponsors and partners, especially the City of Highland Park, First Bank of Highland Park, and the Highland Park Community Foundation. 🙏🏼

🎨: Karol Skoczen & 

   

06/10/2026

SOUND ON! Sneak peak of Bitter Jester Music Fest Night 3: June 12 @ 5:30pm! Discover your next favorite band this summer in

🎸In Competition on Night Three:


music
ariband

🎙️Featured Showcases on Night Three:


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🎤Guest Artists on Night Three:


willa_zatzenbloom

44 bands & soloists from two dozen states descend upon Chicagoland for Bitter Jester this season. So come on out and kick back with a cool drink or grab a bite to eat as you find some incredible new artists to add to your Spotify when you leave the festival.

Night Three Judges (all BJMF alumni!) are:

•Lauren Blackford (2024 Finalist & Vocalist of the Year)
•Damian Kessler (2023 Grand Champion & Drummer of the Year)
•Logan Lake (2019 Runner-Up & Drummer of the Year)
•Taylor Parks (2008 Competitor & 2012 Finalist)
•John Williams (2013 Grand Champion)

… with Nicolas DeGrazia (BJMF Founder & Producer) & Michael Tseitlin (3-time Honorable Mention) providing verbal commentary for the bands!

Huge thank you to our sponsors and partners, especially the City of Highland Park, First Bank of Highland Park, and the Highland Park Community Foundation. 🙏🏼

🎨: Karol Skoczen & 

   

We had such wonderful audiences on our first weekend of the 20th anniversary of Bitter Jester! Thank YOU for supporting ...
06/09/2026

We had such wonderful audiences on our first weekend of the 20th anniversary of Bitter Jester! Thank YOU for supporting live music and upcoming artists. We still have even more talent to come out and see at Port Clinton Square this weekend, you won’t want to miss it!

For the third year in a row, the Chicago Botanic Garden has invited the Bitter Jester Music Festival to kick off its Mus...
06/09/2026

For the third year in a row, the Chicago Botanic Garden has invited the Bitter Jester Music Festival to kick off its Music on the Esplanade series. Tonight featured BJMF 2026 Guest Artist Violet Clare followed by Zack Fedor and The Long Goodbyes. The garden patrons were up and dancing for both sets and we can’t wait to have more great music back again next week!
🪻🧡

06/06/2026

A message from Peter Sagal, host of “Wait Wait… Don’t Tell Me!” on NPR about the Bitter Jester Music Fest, north of Chicago! Come out to the concerts in Highland Park this season (June 5, 6, 12, 13, and 27) or catch the livestreams each night! Peter returns as Co-Host of the June 27 Grand Finale alongside festival founder Nicolas DeGrazia. 🎶DISCOVER YOUR NEXT FAVORITE BAND AT BITTER JESTER🎶

Huge thank you to this year’s major sponsors:          /    —

Special shout-out to our partners          &  … we couldn’t do this without you. Also much love to   &  for past support 🫶🏼

06/04/2026

SOUND ON! Sneak peak of Bitter Jester Music Fest Night 2: June 6 @ 5:30pm! Discover your next favorite band this summer in

🎸In Competition on Night Two:


mckennatheattic_



🎙️Featured Showcases on Night Two:


lily.band

🎤Guest Artists on Night Two:




44 bands & soloists from two dozen states descend upon Chicagoland for Bitter Jester this season. So come on out and kick back with a cool drink or grab a bite to eat as you find some incredible new artists to add to your Spotify when you leave the festival.

Night Two Judges (all BJMF alumni!) are:

•Todd Kiefer (Two-Time Grand Champ)
•Mariah Conway (2017 Vocalist of the Year)
•Alex Johnson (Two-Time Grand Champ & 2022 Guitarist of the Year)
•Talitha “TT” Miller .tempos (former Competitor)
•Andrew Vucsko-Cameron (2024 Grand Champ)

… with Mackenzie Bufis (Music Educator and Exec & Michael Tseitlin (3-time Honorable Mention) providing verbal commentary for the bands!

Huge thank you to our sponsors and partners, especially the City of Highland Park, First Bank of Highland Park, and the Highland Park Community Foundation. 🙏🏼

🎨: Karol Skoczen & 

   

06/04/2026

SOUND ON! Sneak peak of Bitter Jester Music Fest Night 1: June 6 @ 5:30pm! Discover your next favorite band this summer in

🎸In Competition on Night One:




summer


🎙️Featured Showcases on Night One:
band
bandofficial

🎤Guest Artists on Night One:




44 bands & soloists from two dozen states descend upon Chicagoland for Bitter Jester this season. So come on out and kick back with a cool drink or grab a bite to eat as you find some incredible new artists to add to your Spotify when you leave the festival.

Huge thank you to our sponsors and partners, especially the City of Highland Park, First Bank of Highland Park, and the Highland Park Community Foundation. 🙏🏼

🎨: Karol Skoczen & 

   

05/28/2026

Kathleen takes us on a quick 2-min tour of the Halftone Agency’s press making this year’s Bitter Jester Shirts! has an impressive track record working with bands and music festivals and are located right in Chicago! Not only is Halftone proud to be a sponsor for the Bitter Jester Music Fest this year, they also offered a printing discount to all the artists who applied to the festival this season!

Fun fact: An accomplished musician herself, Kathleen has been a satellite series performer many times with Bitter Jester’s shows and, more recently, has been a judge for several seasons!

Special shout-outs to Sunset Foods and Bluegrass Restaurant, our other two t-shirt sponsors this season! They enable BJMF to provide all judges and volunteers with a free shirt and this printing wouldn’t have been possible without their generosity and belief in what the festival stands for

Address

600 Central Avenue
Highland Park, IL
60035

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