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 the full season of events at the brand-new outdoor event space, The Lot, in Downtown Highland Park, the Ravinia District’s Food Truck Thursdays to the award-winning Port Clinton Art Festival, there’s something for everyone this summer in Highland Park.
The Lot
An exciting new season of festivals is coming to The Lot! Be sure you’re signed up for The Weekender newsletter to be the first to see the lineup.
Food Truck Thursdays
The charming Ravinia District’s Food Truck Thursdays event series will return June 6, 2024! 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 Wednesday, 7 AM - 1 PM at Jens Jensen Park. Each week, enjoy music and pop-up vendors providing services such as knife and scissor sharpening.
Bitter Jester Music Festival
FRI / SAT, JUNE 7, 8, 14, & 15 | 6:00 PM | PORT CLINTON SQUARE
GRAND FINALE - SAT., JUNE 29 | 2:00 PM | THE LOT
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!
As 101.9 The Mix put it: "Come out and say hi! It's going to be an incredible concert with a bunch of future headliners!" So check out some of your next favorite bands and be able to say "I saw them when..."
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 Square is located at 600 Central Ave. in downtown Highland Park.
The Lot is located at the intersection of St Johns and Central Avenues in Highland Park.
Port Clinton Art Festival
August 24 - 25 | 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 250 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 250 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, August 12 - Saturday, August 13
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 2 | 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.