Downtown Concerts at Port Clinton
Fridays, July 10 - September 25
Port Clinton Square | 600 Central Ave.
Free, City-produced Friday night concerts at Port Clinton Square return for a third year! Mark your calendars for 10 Friday evenings, July 10 - September 25.
Bring a lawn chair and start your summer weekends with live music and fun for the entire family. On-site food and beverage vendors will round out this local Friday-night favorite event. Stick around for an exciting extended season finale on September 25 featuring the return of the ever-popular Scarecrow Trail through Downtown Highland Park for attendees to vote “best in show!” Concerts will generally run 6 PM - 8 PM.
*Please note there will be no concerts July 24 or August 28, the July 10 concert will be 5 PM - 7 PM, and the finale concert on September 25 will be 4 PM - 8 PM.
Get ready for more music, more food, and more fun in 2025!
New for 2026: Take a trip around the world without ever leaving Highland Park this summer. Each week, partake in global cuisine from an onsite local Highland Park restaurant while enjoying accompanying world music. No passport necessary.
Want to get your weekend concerts started early? The Bitter Jester Music Festival will hold preliminary concerts June 5, 6, 12, and 13 at Port Clinton Square. The Grand Finale on June 27 will take place on Second Street in Downtown Highland Park. While not part of the City’s official EnjoyHP Events lineup, and not produced by the City of Highland Park, the Bitter Jester Music Festival is a landmark on Highland Park’s music scene. 2026 marks 20 years of talented youth performers sharing their passion with HP. The City invites you to take part in this iconic festival.
2026 Entertainment & Vendor Lineup
Check back soon for more information. If you would like to participate as a vendor, please contact the City’s contracted event management team, Ripple Public Relations, at info@ripplepublicrelations.com or 847.432.6000. If you would like to participate as a performer, please contact the City’s contracted music manager, United Talent Coordinators at joey@unitedtalentco.com.
2026 Finale & Scarecrow Trail
Friday, September 25| 4 PM - 8 PM
Wrap up the 2025 Downtown Concert series with a fun fall afternoon. Interact with giant, live scarecrow puppets at Port Clinton Square and jam out to awesome tunes.
Check back soon for more information. If you would like to participate as a performer or vendor, please contact the City’s contracted event management team, Ripple Public Relations, at info@ripplepublicrelations.com or 847.432.6000
Getting to the Downtown Concerts at Port Clinton Square & Parking
Downtown Concerts at Port Clinton Square will take place at Port Clinton Square (600 Central Ave.).
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 Lot and in the immediate vicinity, and the Metra is a viable option, too. Information about parking in the City of Highland Park is available here.
Downtown Highland Park is also 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.
Thank You to Our 2026 Sponsors!
For sponsorship opportunities and packages, please contact Ripple Public Relations - info@ripplepublicrelations.com / 847.432.6000