The Bitter Jester Music Festival (BJMF) returns for its 20th season of live concerts this summer (2026)!

This is a FREE, family-friendly concert series with FREE PARKING! BJMF is recognized for showcasing over 150 exceedingly talented emerging musicians from across the Midwest each year at its free weekly 5:30 p.m. concert series in Downtown Highland Park’s Port Clinton Square. 2026 Concerts are on June 5, 6, 12 and 13.

The festival is a competition where bands of all shapes and sizes as well as solo musicians compete in front of live audiences and industry judges.

To celebrate the 20th Anniversary, all of the judges this summer will be returning Bitter Jester alumni who will select a winner each week. The four winners – plus four additional “Wild Card” bands selected by BJMF producers – will advance to a Grand Finale Concert on June 27, 2026, at a concert to be held on Second Street, between Central and Laurel Avenues in Downtown Highland Park. Judges at that event will be former Bitter Jester Grand Champions representing various "eras" going back to 2006.

Cash prizes and other awards are given out after winners are announced at the end of the night.

Applications are open through April 15 (check the BJMF website for more details).

The Grand Prize winner takes home a $2,000 cash prize, the Runner-Up gets $1,000, and $500 goes to Honorable Mention - all courtesy of First Bank of Highland Park.

Wine and craft beer will be available to of-age patrons at all concerts as well as a variety of food for sale.

The June Preliminary Concerts take place at Port Clinton Square (600 Central Ave, Highland Park).

Check the BJMF Instagram for the most up-to-date information or visit their website at www.BitterJesterMusic.org