Highland Park's Summer Concert Series Closes With Scarecrow Trail

HIGHLAND PARK, IL — Highland Park will wrap up its 2026 Downtown Concerts at Port Clinton Square series with the return of the Scarecrow Trail, featuring live performances, food vendors and family activities in the downtown area.

The event is scheduled on Sept. 25 from 4 to 8 p.m. and will center on Port Clinton Square and downtown businesses.

The scarecrow-themed program will include kids’ activities, facepainting, airbrush tattoos, pumpkin crafts, Wizard of Oz characters and larger-than-life scarecrow puppets as Highland Park shifts from its summer concerts into the fall season.

More than two dozen decorated scarecrows are expected throughout the Central Business District, turning downtown into what the announcement described as an “autumn wonderland.” Attendees will be able to explore the displays and vote for “Best in Show Scarecrow” at enjoyhighlandpark.com/scarecrow.

After visiting the downtown displays, attendees can bring lawn chairs to Port Clinton Square for an afternoon and evening of music. The posted lineup includes Miss Jamie’s Farm from 4 to 4:30 p.m., Istvan & His Imaginary Band from 4:45 to 5:15 p.m., Ben Tatar & The Tatar Tots from 5:30 to 6:30 p.m., and Taylor & Mane from 6:30 to 8 p.m.

Glinda and Dorothy from the Wizard of Oz will also be onsite for photos and family interactions, according to the announcement.

The city also listed other upcoming events in its 2026 Enjoy HP series, including Oktoberfest on Sept. 26, Stews & Brews on Oct. 10 and Holiday Lighting on Nov. 22.