2025 Bitter Jester Music Festival - Official Lineup
Discover your next favorite band at Bitter Jester!
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. 🤟🏼🤟🏼
CONCERT DATES:
June 2 & 9 (Showcase Concerts @ Chicago Botanic Garden);
June 6, 7, 13, & 14 (Preliminary Concerts @ Port Clinton Square);
June 28 (Grand Finale in Downtown Highland Park on Second St);
June 18 (Showcase @ Ravinia Festival - Scorched Waves opens for The Black Crowes);
Sept 1 (“Best Of” Concert @ Navy Pier’s Beer Garden)!
Each week, six bands/solo artists from across the Midwest and beyond battle for a spot in the June 28, 2025, Grand Finale for a $2,000 cash prize, gear, incredible additional performance opportunities, and the title of Grand Champion! One BJMF Finalist will be selected to open for a National Headliner at Ravinia Festival in 2026!
These FREE concerts are vibrant and fun variety acts that the whole family can enjoy. You’ll be sure to discover your next favorite band or solo artist to add to your personal playlists after the festival!
Friday, JUNE 6, 2025
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!)
• BYRON (Guest Artist)
• Charlieboy
• The Coves
• Earl Hester (Showcase)
• Holden Garcia (Guest Artist)
• Meera Raphael
• Nikki Rodrigues (Guest Artist)
• North Grove
• The Reys
• Silver October (Guest Artist, MUSIC @ 5:15pm)
• Speedbump
• State of Youth (Showcase)
Saturday, June 7, 2025
Port Clinton Square - 5:30pm (rain or shine!)
600 Central Ave, Highland Park, IL, 60035
6/7/25 Official Lineup:
Click to read Performers’ / Judges’ Bios (and listen to a mashup of the night’s performers!)
• The 1-800s
• Ayden Holt (Guest Artist)
• The Broken Vinyls
• Claire-Mckenna
• Holden Garcia (Guest Artist)
• NewClearFusion (Showcase)
• Patches & Albo
• Superimposed
• Tikimen of Berlin
• Trial and Error (Showcase)
• Violet Clare (Guest Artist)
Friday, JUNE 13, 2025
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!)
• Candy Cigarette (Showcase)
• Christine Compall (Guest Artist)
• Floryence (Guest Artist)
• Lackadays
• Monica James (Guest Artist)
• Plastic Summer
• Platinum Moon
• The Regulars
• Sierra Sikora
• STARLESS (Showcase)
• ZEKE ROWAN
Saturday, June 14, 2025
Port Clinton Square - 5:30pm (rain or shine!)
600 Central Ave, Highland Park, IL, 60035
6/14/25 Official Lineup:
Click to read Performers’ / Judges’ Bios (and listen to a mashup of the night’s performers!)
• Belle Vista (Showcase)
• Cabin Fever
• Control the Sound (Showcase)
• Crowd Vulture
• Elle of the Wilds (Guest Artist)
• Exit 122
• The Orchids
• Party Hat Club
• rae
• TUMI (Guest Artist)
sATURday, June 28, 2025
(Grand Finale)
Downtown Highland Park on Second St. - 2:00pm (rain location TBA)
Between Central & Laurel in Highland Park, IL 60035
6/28/25 Official Lineup - to be announced throughout June
• TBA
• TBA
• TBA
• TBA
• TBA
• TBA
• TBA
• TBA
• TBA
• TBA
• TBA
• TBA
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, 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.
(Full Grand Finale Lineup Announced in Late June!)
Click here for more detailed 2024 Grand Finale concert info!