Highland Park 2025 Downtown Event Season

Over the past three years the City has presented over 20 free events that brought over 75000 visitors to Highland Park creating vibrancy enhanced business patronage and community involvement in and around town. As plans progress the eclectic line-up of events planned for 2025 throughout downtown Highland Park include:

• Taste of Highland Park: June 20 & 21 5-10 PM

Kick off the event season with the Taste of Highland Park the City’s premier food and music festival. Sample more than a dozen local food and beverage vendors and taste what sets Highland Park apart on the North Shore. Enjoy an eclectic lineup of live music spanning multiple decades and genres be mesmerized by local performing arts groups and take part in a variety of on-site fun for the entire family! This can’t-be-missed event will take place at Port Clinton Square (600 Central Ave.) and along Central Ave. between First and Second Streets. Stay tuned for a full line-up of vendors and entertainment coming soon!

• Downtown Concerts at Port Clinton Square: July 11 - September 26 6-8 PM

The City of Highland Park is thrilled to announce the return of free City-sponsored downtown concerts at Port Clinton Square (600 Central Ave.). Bring a lawn chair or blanket and kick-off a summer weekend with live music in a variety of genres (including performances from Highland Park based performing arts groups) and fun for the entire family. There will be on-site food and beverage vendors and an exciting extended season finale on September 26 featuring a festive Scarecrow Trail through downtown Highland Park in which attendees can vote for “best in show!”

*Please note there will be no concert July 22 or August 22

• Vintage Car Show: September 6 12-4 PM

Step back in time and experience the elegance craftsmanship and the nostalgia of a bygone era with the Vintage Car Show! Spend the day in Highland Park’s vast St. John’s Parking Lot (525 Central Ave.) perusing an eclectic display of vintage antique and classic vehicles pop culture icons hot rods muscle cars and more all while enjoying a live radio broadcast food and libations from local vendors and kid-friendly activities. 

• Stews & Brews: October 11 5-9 PM

This cool weather fan-favorite event will warm the hands and stomachs of all who attend! Stews & Brews features a variety of hearty stick-to-the-ribs stews including chili jambalaya Hungarian goulash chicken pot pie and more; if it is a warm meal in a bowl it qualifies! All kinds of brews will be available too from craft beer spiced ciders and wines to hot toddies and kombucha! Enjoy stellar live entertainment from the stage while staying warm and cozy by fire pits and heat towers at Port Clinton Square (600 Central Ave.) and along Central Avenue. Stay tuned for a full line-up!

Host or Publisher Ripple Public Relations