Events & Festivals
Events & Festivals
Highland Park’s seasonal calendar of events offers great opportunities to visit, whether you’re planning to spend a few hours or an entire day. From concerts, car shows, and food festivals in Downtown Highland Park, the Ravinia District’s Food Truck Thursdays and Farmers Markets, to the award-winning Port Clinton Art Festival, there’s something for everyone year round in Highland Park.
Downtown Events
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.
Food Truck Thursdays
The charming Ravinia District’s Food Truck Thursdays event series will return June 5, 2025! Sign up for The Weekender newsletter to be the first to hear about the music schedule. The lineup of food trucks changes weekly, and vendors include Highland Park restaurants, North Shore favorites, and Chicago eateries.
Ravinia Farmers Market
Shop a wide variety of fresh fruits, vegetables, meats, cheeses, and flowers at the Ravinia Farmers Market every Saturday from 10 AM - 2 PM at Wayfarer Theaters (1850 Second Street) during the winter from January 11 - April 26. Then, head to Jens Jensen Park every Wednesday from 7 AM - 1 PM, from June 4 - October 29 for the summer market. Each week, enjoy music and pop-up vendors providing services such as knife and scissor sharpening.
Bitter Jester Music Festival
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 at The Lot.
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.
Port Clinton Art Festival
August 23 - 24 | 10 AM - 5 PM
The Port Clinton Art Festival, one of the country’s top festivals, returns to Highland Park offering fine art from more than 200 of the world’s most celebrated artists. Throughout the weekend festival-goers will have the opportunity to enjoy interactive art demos and, of course, original artwork offered by master artists from around the world. In addition to 200 Juried Artists, there will be an Emerging Artist Section! The Port Clinton Art Festival is produced by Highland Park-based company Amdur Productions.
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Sidewalk Sale
Friday, July 25 - Saturday, July 26
Shop great sales from boutique shops throughout Highland Park’s downtown shopping district. The Sidewalk Sale is sponsored by the Highland Park Chamber of Commerce.
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National Night Out
August 5 | 6:30 PM | City Hall
Enjoy family-friendly activities, including an obstacle course, drone display, bike safety checks and Touch-a-Truck at this special event sponsored by the Highland Park Police Department.