Downtown Events
Get excited for a new season of alfresco dining and live, family-friendly entertainment in the heart of downtown Highland Park
A dynamic lineup of special events and festivals returns to Downtown Highland Park beginning June 2025! Discover unique local dining, family-friendly entertainment, and weekend concerts. Check back soon for event details, music lineup and more!
For more information on how to be a part of the 2025 Downtown Highland Park event season as a participating vendor or sponsor, please contact the City’s event management team, Ripple Public Relations, info@ripplepublicrelations.com, or call 847.432.6000.
2025 Event Lineup
Friday, June 20 & Saturday, June 21, 5 PM - 10 PM both days
Port Clinton Square (600 Central Ave.) & Central Ave. between First and Second St.
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 local Highland Park restaurants, all while jamming out to exceptional live entertainment themed around music’s biggest decades; the 70s, 80s, 90s, and 00s. Stay tuned for 2025’s vendor and entertainment lineup.
Select Friday evenings July 11 - September 26, 6 PM - 8 PM
Port Clinton Square (600 Central Ave.)
We’re excited to bring you an extended season featuring 10 Friday evening concerts*, performances from a variety of artists and genres (including special performances by Highland Park performing arts groups), on-site food and beverage vendors, and an exciting extended finale on September 26 featuring a festive scarecrow trail through Downtown Highland Park.
*No concerts July 25 or August 22
Saturday, September 6, 12 PM - 4 PM
St. Johns Parking Lot (525 Central Ave.)
Step back in time and experience the elegance, craftsmanship, and the nostalgia of a bygone era. Relive the golden age of automobiles at the Vintage Car Show on Saturday, September 6. Head to the St. John’s lot (525 Central Ave.) and peruse a fabulous array of vintage vehicles, while enjoying a live radio broadcast, kid-friendly activities, delicious food, and ice cold beverages.
Saturday, October 11, 5 PM - 9 PM
Port Clinton Square (600 Central Ave.) & Central Ave. between First and Second St.
Stews & Brews returns to Downtown Highland Park for a fourth season! This HP-exclusive event combines 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!
Getting to Downtown Events & Parking
Ample parking can be found throughout downtown Highland Park, including a parking garage underneath Port Clinton Square, nearby surface lots, a parking lot along St. Johns Ave., and a two-level parking deck south of Central on First St. and St. Johns. The City encourages guests to use non-motorized transportation where available. Bike racks are available at the St. Johns parking lot (525 Central Ave.) and in the immediate vicinity. Metra trains and Pace busses are other viable options.
More information about parking in the City of Highland Park is available here.
Downtown Highland Park is easily accessible via public and non-motorized transport.
Metra - take UP-N to the Highland Park station, located a 4 minute walk from The Lot.
Pace Bus - take Highland Park/Highwood Route 472 to the St. Johns/Central stop, across the street from The Lot.
Bike/Walk - from the north, take the Robert McClory Bike Trail south to Vine Ave. Head east on Vine, turning south onto St. Johns Ave. From the south, take the Robert McClory Bike Trail north along St. Johns Ave. Bike racks are available at The Lot and in the immediate vicinity.
Taste of Highland Park, Downtown Concerts at Port Clinton, and Stews & Brews - 600 Central Ave.
Vintage Car Show - 525 Central Ave.
Thank You to Our 2025 Sponsors!
For sponsorship opportunities and packages, please contact Ripple Public Relations - info@ripplepublicrelations.com / 847.432.6000