Woodstock Art Fair on the Square

About

Woodstock Art Fair on the Square is an outdoor juried art festival produced by Amdur Productions, filling Downtown Woodstock Square with 75 original artists. The fair is free to enter with free parking, and the historic square, its restaurants and its shops all stay open through the weekend.

2026 edition

• Dates: Saturday 3 and Sunday 4 October 2026
• Hours: 10 a.m. - 5 p.m. daily
• Venue: Woodstock Square, 121 W Van Buren St, Woodstock, IL 60098, United States (near the Woodstock Metra station)
• Format: 75 exhibiting artists with listed booth numbers; live music; live art demonstration signs
• Family programming: Kids Art Zone with art fest bingo, spin art, sand sculpture, colouring and drawing, plus a face painting tent
• Visitors can enter a draw for a $100 Art Fest gift card, and spend it with artists at the festival

Organizer

Amdur Productions, based at 2115 Green Bay Rd, Highland Park, IL 60035 (847-926-4300), runs a season of juried art festivals across the Chicago area; artist applications, booth assignments and festival policies are all handled through its site.

Notes

• The same fair name is used by a different event: Art Fair on the Square is the Madison Museum of Contemporary Art's long-running July fair in Madison, Wisconsin. This entry is the Woodstock, Illinois festival.
• The domain artfaironthesquare.com now also lands on this Woodstock fair.