Street Art Fest 2027

Street Art Fest 2027 is an annual street-painting and community arts festival centered on Highland’s downtown Square in Highland, Illinois. Scheduled for Saturday, September 18, 2027, it combines a judged chalk-art competition with a Makers Market, live entertainment, food and drinks, and children’s activities.

The streets become the gallery

The festival’s centerpiece is artists creating large, temporary works directly on the pavement with chalk, letting visitors watch pieces develop throughout the day. The 2027 competition runs from 9 a.m.–4 p.m., followed by judging at 4 p.m. and awards at 5:30 p.m.; the overall festival runs 11 a.m.–6 p.m.

More than a chalk competition

Street Art Fest is designed as a broader downtown arts celebration. The Makers Market runs throughout the festival with locally made goods such as pottery, jewelry, candles, fiber crafts and décor, while local bands and dance or cheer groups provide entertainment; food and drink vendors round out the event.

Family activities

The Kreative Kids Korner is scheduled from 11 a.m.–5 p.m., with opportunities for children to make art, play games and use a bounce house. The festival page also highlights the returning Monster Mural, an interactive painting experience connected with Discover Downstate Illinois.

A Highland tradition

The event draws on the centuries-old tradition of street painting while giving it a distinctly local character. Recent editions have brought together dozens of professional and amateur artists, and the Highland Chamber of Commerce uses the festival both to celebrate regional creativity and to support Chamber programs and local-business initiatives.