Welcome to the 2026 Bitter Jester Music Fest!
We’re glad you here. You’ll be sure to discover your next favorite band at Bitter Jester in Downtown Highland Park this summer.
FREE CONCERTS • FREE PARKING • FAMILY-FRIENDLY
What on Earth is the Bitter Jester Music Fest? It’s a free concert series. It’s a charity event. It’s a volunteer-run passion project. It’s a live album recording session. It’s a movement. It’s the place you want to be this summer for great live music, delicious beer and hot or cold coffee, and a good time for not a lot of money. BJMF was voted Best Small Festival in the 2025 Festy Awards!
New band plays every 30 minutes!
A message to the North Shore from NPR’s Peter Sagal!
Click to read Performers’ / Judges’ Bios (and preview each night’s lineup in a Spotify Playlist)!
2026 CONCERT DATES:
June 5, 6, 12, & 13 (Preliminary Concerts @ Port Clinton Square, 5:30-10:30pm);
June 8 & 15 (Showcase Concerts @ Chicago Botanic Garden, 6-7:30pm);
June 27 (Grand Finale in Downtown Highland Park on Second St, 2-10pm);
Aug 22 (Showcase @ Ravinia Festival - Scorched Waves opens for The Black Crowes, 5pm);
Sept 7 (“Best Of” Concert @ Navy Pier’s Beer Garden, 1:20-8pm)!
If you enjoy great FREE concerts with FREE parking, come support our volunteer-run non-profit music festival with a donation in place of your ticket. 🤟🏼🤟🏼
Each week, 11 bands/solo artists from across the country take center stage with six of them battling for a spot in the June 27, 2026, Grand Finale co-hosted by Peter Sagal (host of “Wait Wait… Don’t Tell Me!” on NPR). Up for grabs is a $3,000 cash prize, gear, incredible additional performance opportunities, and the title of Grand Champion! One Finalist will be selected to open for a National Headliner at Ravinia Festival in 2027!
These FREE concerts are vibrant and fun variety acts that the whole family can enjoy without breaking the bank. You’ll be sure to discover your next favorite band or solo artist to add to your personal playlists after the festival! BJMF was founded by Highland Park native and Emmy-winning Director Nicolas DeGrazia.
As a 501(c)(3) nonprofit, your donations are HUGELY appreciated and directly go toward sustaining and improving this music fest!
Bitter Jester Music Fest has been a proven feeder festival for Lollapalooza, Ravinia Festival, RiotFest, and SXSW. What’s more, this FREE weekend concert series of live music makes a great and fun activity for the whole family to enjoy! Looking for weekend plans and fun things to do? Look no further than Bitter Jester.
The Bitter Jester Music Festival is sponsored by the City of Highland Park and supported by small grants from the Highland Park Community Foundation and the IL Arts Council Foundation. All Grand Finale Prize Money is generously donated by First Bank of Highland Park, our Prize Money Sponsor. Additional support from Ludwig Drums, Humes & Berg, Shure, Sweetwater Sound, Judy’s Pizza, and Elmore Pedals.