2024 Season Lineup

Taste of Highland Park
Friday, June 21 & Saturday, June 22, 5 PM - 10 PM both days
Highland Park’s premier food and music festival returns with more music, more food, and more fun! Savor the taste of summer with special dishes and select beverages curated from Highland Park restaurants, all while jamming out to exceptional live music from headliners Nine Days, Dishwalla, and Spin Doctors.

Vintage Car Show
Sunday, August 11, 12 PM – 4 PM
Peruse a fabulous array of vintage vehicles, right on St. Johns Avenue while enjoying a live radio broadcast with famed DJ Eddie “V,” and snacking on delicious food and beverages.

NEW - Decades
Saturday, September 14, 12 PM – 10 PM
Fantastic headlining music from the 70s, 80s, and 90s brings together decades of music fans. Travel back in time to experience the sounds, tastes, and trends from these three decades through a selection of live performances and food and beverage vendors. A “Decades of Music” interactive trail through downtown Highland Park businesses adds an air of adventure to this nostalgia-filled event. Stick around for a drone show once the sun goes down!

Oktoberfest
Saturday, September 28, 12 PM – 10 PM
Start the day with traditional Oktoberfest fun: music, food, beverages, and family-focused activities. At 5 PM, we switch up the vibe with a headline band.

NEW - Scarecrow Fest & Walk
Saturday, October 19, 12 - 5 PM
Stroll downtown Highland Park businesses to view festive, decorated scarecrows. Then head to The Lot to celebrate the season with food, family fun, and Grammy-nominated kids’ performers!

Stews & Brews (& Booze & Blues)
Saturday, November 2, 5 - 9 PM
Combining two Midwestern favorites: comfort foods and beverages. Stay cozy with fire pits, heaters, hearty food, and great live music. The evening culminates with a People's Choice competition for the favorite Stew and Brew. This event is sure to warm the hearts and souls of all who attend!

Also happening at The Lot in 2024…

Bitter Jester Music Festival Grand Finale*
Saturday, June 29, 2 PM - 10 PM
It’s more than a competition, it’s a destination event, complete with music, food, and beverages. A dozen musical acts showcase their virtuosity at The Lot, competing for the title of Grand Champion. Many BJMF alumni have gone on to perform on Late Night with Seth Myers, Saturday Night Live, and American Jukebox, as well as at Lollapalooza, Riot Fest, South by Southwest, and Ravinia Festival. Discover your next favorite band at the 18th Annual Bitter Jester Music Fest and be able to say "I saw them when..."

*This event is produced by a nonprofit charity and hosted by the City of Highland Park