Art Fair on the Square

September 20 & 21, 2025 | 10AM-5PM

The Woodstock Art Fair on the Square returns September 20–21 with a full weekend of creativity and fun in our Historic Square! Explore the work of 75 original artists, enjoy live music, and see amazing art pieces showcased on the beautiful Historic Woodstock Square.

Be sure to stop by the Chamber’s Beverage Station on Johnson Street to grab a refreshing drink while you stroll the art and enjoy the festivities!

Highlights:

• Shop from 75 original artists

• Enjoy live music all weekend

• Take a live painting class

• Explore the Kids Art Zone with spin art, sand sculpture, coloring & more

• Become living art at the Face Painting Tent

• Watch artists at work with Live Art Demos

• Stroll an accessible, family-friendly festival

• Just steps from the Woodstock Metra Station

• Free admission & free parking

Interested in volunteering at the Chamber's beverage station? Click the button below to sign up!