Bitter Jester Music Festival
2026 PRELIMINARY CONCERTS
FRIDAY / SATURDAY, JUNE 5, 6, 12, & 13 | 5:30 PM - 10:30 PM | PORT CLINTON SQUARE
2026 GRAND FINALE CONCERT
SATURDAY, JUNE 27 | 2 PM - 10 PM | SECOND STREET BETWEEN CENTRAL AVE. & LAUREL AVE.
Discover your next favorite band at Bitter Jester, Highland Park's other great music festival! Sponsored by the City of Highland Park, IL, This free, family-friendly concert series has been taking place in Downtown HP annually since 2006. What started as a small "battle of the bands" for local performers has evolved into the nation's largest live festival showcasing emerging artists under the age of 25. Hundreds of performers from all across the nation apply every winter/spring and the festival invites about 40 musical acts from over a dozen states to perform. A "battle of the bands" style event (featuring the top 20% of applicants) has the top acts vying for almost $15,000 in cash and other prizes. With food, craft beer, wine, great coffee, and free parking, the Bitter Jester Music Fest is a must-see event in Downtown Highland Park!
Multiple genres are featured each night with musicians receiving highly detailed feedback from industry professionals in the process. A winner is selected at each of four Preliminary Concerts with four additional "Wild Cards" selected by Festival Producers. Those eight acts then compete head to head at a Grand Finale Concert co-hosted by Nicolas DeGrazia (an Emmy-winning TV director and HP native - the festival's founder) and Peter Sagal (host of "Wait Wait... Don't Tell Me!" on NPR). Come to the Finale for the music and stay to hear Peter interview performers after their sets!
As 101.9 The Mix put it: "It's 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.
Stay tuned for additional details regarding the 2026 Bitter Jester Music Festival.
About the Festival
Established in 2006, the Bitter Jester Music Festival (BJMF) is an official City of Highland Park sponsored event that has been running annually for over 20 years. BJMF was named "Best Small Festival" in the 2025 Festy Awards, which honors "the best in live music and festivals" across the country. The festival is produced by the 501(c)(3) nonprofit Bitter Jester Foundation for the Arts, a public charity based in Illinois that was also the 2024 recipient of the Highland Park Arts Award. As the Midwest’s largest professional multi-state music competition and concert series for emerging musicians, BJMF supports and promotes young and up-and-coming talent from across the country. For the audiences, BJMF is a showcase of some of the best new bands of today - the festival's slogan is "Discover Your Next Favorite Band at Bitter Jester" for good reason. Behind the scenes, the event emboldens and empowers young adults at a critical time in their social and artistic development. Participating musicians receive unparalleled quantities of educational feedback (written, verbal, and audio commentary), photo and video support, networking opportunities with industry professionals & working musicians, and connections to larger venues like Ravinia Festival, Navy Pier, the Chicago Botanic Garden, and many more.
Music
The Bitter Jester Music Festival is genre-agnostic, featuring everything from solo acoustic to indie rock to rap to death metal and everything in between. Every night of the festival features 9-12 artists spanning a wide variety of sonic stylings. Congratulations to this year's musicians! For current lineup information or to learn more about upcoming seasons of the Bitter Jester Music Festival, visit www.BitterJesterMusic.org.