Downtown Events Series

An exciting new season of festivals, amazing live music, and delicious food is planned for 2025! Get ready for the Taste of Highland Park on June 20 & 21, the Vintage Car Show on September 6, and Stews & Brews on October 11. Plus, enjoy 10 fantastic Friday night concerts at Port Clinton Square between July 11 and September 26. Further details on participating artists and restaurants will be released soon. Sign up for the Weekender enewsletter to get the details sent right to your inbox.

Port Clinton Square lights up on November 22, 2025 from 4 PM - 6 PM. See the tree, menorah, and square spring into holiday cheer. Meet your favorite characters like Santa, Hanukkah Harry, and Elsa & Anna from Frozen. Take family photos in one or more of the festive holiday vignettes set up around the square. Have your face painted with a cheery holiday design. Listen to your favorite tunes spun by DJ Julian, plus be serenaded by the Frozen Robin Carolers and the Highland Park High School Choir. Enjoy complimentary popcorn and hot chocolate. This free event is the perfect way to kickoff the holidays.

Discover your next favorite band at Bitter Jester! This free, family-friendly concert series has been taking place in Downtown Highland Park since 2006. What started as a small "battle of the bands" for local performers has evolved into the Midwest's largest showcase for emerging artists. With performers coming from nearly a dozen states and vying for $3,500 in cash prizes, the Bitter Jester Music Fest is a must-see event!
Multiple high-quality acts perform each night and receive detailed feedback from industry professionals. A winner is selected at each of the four Preliminary Concerts and four "Wild Cards" are chosen at the end of the summer by Festival Producers. Those eight acts then compete at a Grand Finale Concert.

Select Bitter Jester Finalists are chosen to open for national headliners on Ravinia's Carousel Stage and also perform a "Best Of" show at Navy Pier's Beer Garden on Labor Day each year.