The Bitter Jester Music Festival (BJMF) returns for its 19th season of live concerts this summer (2025)!

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. 2025 Concerts are on June 6, 7, 13, and 14.

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.

A panel of music and media professionals 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 28, 2025, at a location TBA.

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.

The 2025 season will feature over 150 musicians representing 50+ cities and three dozen bands including non-competing showcase artists from across Lake County and the entire Midwest.

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).

The June 28 Grand Finale location will be announced later in the season (check the BJMF Instagram for the most up-to-date information).

More information at www.BitterJesterMusic.org