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.
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Events in Downtown Highland Park
EnjoyHP Events Series
An exciting new season of festivals, amazing live music, and delicious food is planned for 2026! Get ready for the Taste of Highland Park on June 19 & 20, the Vintage Car Show on August 22, the return of Oktoberfest on September 26, and Stews & Brews on October 10. Plus, enjoy 10 fantastic Friday night concerts at Port Clinton Square between July 10 and September 25. 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.
Holiday Lighting
Port Clinton Square lights up on November 21, 2026 from 4 PM - 6 PM. See the tree, menorah, and square spring into holiday cheer. Meet your favorite characters like Santa, Hanukkah Harry, and others. Take family photos in one or more of the festive holiday vignettes set up around the square. This free event is the perfect way to kickoff the holidays.
Bitter Jester Music Festival
Port Clinton Art Festival
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 August 22 - 23, 2026. 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.
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.
Events in the Ravinia District
Food Truck Thursdays
The charming Ravinia District’s Food Truck Thursdays event series will return June 4, 2026! 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 Farmer’s Market
Shop a wide variety of fresh fruits, vegetables, meats, cheeses, and flowers at the Ravinia Farmers Market year round! Stay cozy with two indoor winter markets at Wayfarer Theaters (Saturdays, 10:30 AM - 2:30 PM from January 10 - April 25) and Braeside Market (Fridays, 10:30 AM - 2:30 PM from January 16 - April 24). Then, head to Jens Jensen Park every Wednesday from 7 AM - 1 PM, from June 3 - October 28 for the summer market. Each week, enjoy music and pop-up vendors providing services such as knife and scissor sharpening.
Candy Stroll
The annual Ravinia District Halloween Candy Stroll will take place on Friday, October 23, 2026! Visit participating businesses for trick-or-treating and tons of fun. Start your journey at Jens Jensen Park (540 Roger Williams Avenue). The fun will take place from 3:30 PM - 5 PM.
Cookie & Cocoa Crawl
Head back to Jens Jensen Park on December 5, 2026 to kick off the holidays with the annual Cookie & Cocoa Crawl. Visit participating businesses from 11:30 AM - 1 PM for warm cocoa, festive cookies, and tons of fun. Plus, visit with Santa and enjoy holiday tuns spun by a live DJ.
Ravinia District events are presented by the City of Highland Park and the Ravinia District Special Service Area 17 property owners.
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Sidewalk Sale
Friday, July 24 - Saturday, July 25
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 4 | Time & location TBD
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.