2026 Bitter Jester Music Festival - Official Lineup
Discover your next favorite band at Bitter Jester!
FREE CONCERTS • FREE PARKING • FAMILY-FRIENDLY
New band plays every 30 minutes!
Click to read Performer Bios (and listen to a mashup of each night’s bands!)
Looking for something fun to do on the weekend? How about live music near you…
Do you enjoy great FREE concerts with FREE parking? Please support our volunteer-run non-profit music festival with a donation in place of your ticket. 🤟🏼🤟🏼
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)!
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!
Friday, JUNE 5, 2026
Port Clinton Square - 5:30pm (rain or shine!)
600 Central Ave, Highland Park, IL, 60035
6/5/26 Official Lineup:
Click to read Performers’ / Judges’ Bios (and listen to a mashup of the night’s performers!)
• Ambiance (Showcase)
• Belle Vista
• Claim Ursa
• Exit 122
• Holden Garcia (Guest Artist)
• Left For Last
• Madeline O'Dell (Guest Artist)
• Plastic Summer
• The Industrialists (Showcase)
• Versus Vitality
• Youth (Showcase)
Saturday, June 6, 2026
Port Clinton Square - 5:30pm (rain or shine!)
600 Central Ave, Highland Park, IL, 60035
6/6/25 Official Lineup:
Click to read Performers’ / Judges’ Bios (and listen to a mashup of the night’s performers!)
• Cabin Fever
• CARAVAN
• Claire-Mckenna
• Cruze Campo (Showcase)
• Elle of the Wilds (Guest Artist)
• In The Attic
• Liam Sheridan (Guest Artist)
• Naüvoo (Showcase)
• Sierra Sikora
• Spider Lily (Showcase)
• Taranis
Friday, JUNE 12, 2026
Port Clinton Square - 5:30pm (rain or shine!)
600 Central Ave, Highland Park, IL, 60035
6/12/25 Official Lineup:
Click to read Performers’ / Judges’ Bios (and listen to a mashup of the night’s performers!)
• Billy Schaumann
• Briley (Guest Artist)
• Fank! (Showcase)
• Hammerhedd
• Mystik
• Palm Of Your Hand (Showcase)
• Party Hat Club (Showcase)
• THREEGON
• Willa Zatzenbloom (Guest Artist)
• Zion Ari
• zoloft
Saturday, June 13, 2026
Port Clinton Square - 5:30pm (rain or shine!)
600 Central Ave, Highland Park, IL, 60035
6/13/25 Official Lineup:
Click to read Performers’ / Judges’ Bios (and listen to a mashup of the night’s performers!)
• Brady Lorince (Showcase)
• Cam Martin & the Lost Hearts
• Intrepid Cat
• Izzy Savides
• Mistrophia
• Resting in Headlights (Showcase)
• Sofia Devitt (Showcase)
• The Strolls
• Tripsitter
• Vincent Casal (Guest Artist)
• Violet Clare (Guest Artist)
sATURday, June 27, 2026
(Grand Finale)
Downtown Highland Park on Second St. - 2:00pm (rain location TBA)
Between Central & Laurel in Highland Park, IL 60035
6/27/26 Official Lineup:
TO BE ANNOUNCED THROUGHOUT JUNE!
Did you know we’re a non-profit? Your donations are HUGELY appreciated and will directly go toward sustaining and improving the music fest!
Bitter Jester Music Fest has been a proven feeder festival for Lollapalooza, Ravinia Festival, RiotFest, SXSW, and others. 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, in part, by the City of Highland Park and First Bank 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, Bluegrass HP, Sunset Foods, Halftone Agency, the Guitar Center Music Foundation, and Elmore Pedals.
And last but not least, thank you to our wonderful QR Code Partner: “ME-QR” for their generosity and incredible product! Check out ME-QR where you can create & customize dynamic QR codes for FREE.