The City of Highland Park will celebrate the start of the fall season with its third annual Scarecrow Fest and the grand finale of the 2026 Downtown Concert Series at Port Clinton Square and throughout downtown on Sept. 25 from 4-8 p.m.

Attendees can stroll through Highland Park’s Central Business District to discover more than two dozen uniquely decorated scarecrows displayed throughout participating downtown businesses and vote for the “Best in Show Scarecrow.”

The celebration continues at Port Clinton Square with family-friendly activities, live music, food and drinks, and fall-themed fun. Activities include face painting, airbrush tattoos, pumpkin crafts, Wizard of Oz characters, including Dorothy and Glinda, and larger-than-life scarecrow puppets.

Live performances will include Miss Jamie’s Farm from 4-4:30 p.m., Istvan & His Imaginary Band from 4:45-5:15 p.m., Ben Tatar & The Tatar Tots from 5:30-6:30 p.m., and Taylor & Mane from 6:30-8 p.m.

Local food and drink vendors will be onsite, with beverages available for attendees 21 and older. Guests are encouraged to bring a lawn chair and enjoy an evening of fall festivities, live entertainment and community fun in downtown Highland Park. Don't miss this festive fall celebration in downtown Highland Park!

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