Woodstock Art Fair on the Square 2026

The Woodstock Art Fair on the Square returns to the picturesque downtown, where the world famous Opera House and historic Old Courthouse Center stand. Woodstock is a classic and eclectic community rich in arts and culture, brimming with local artists, small businesses and engaged residents with a deep appreciation for the arts. This charming community has been an attractive location for TV and filmmakers throughout the years, with dedicated fans celebrating Groundhog Day again and again. All types of art are welcome.

The festival features about 100 spaces in a suburban setting and is good for newbies, with artisans welcome to apply. Artists keep all their sales income from the show. Amdur Productions staff is present on site throughout the entire festival to assist artists from load in to load out, with Saturday morning setup available where artists can drive up to or very close to their booth space. Additional services include booth sitting, close parking for artists at no additional cost, tent and equipment rentals, setup assistance, hotel discounts, overnight security, and a large multi-layered marketing plan with digital advertisements, radio, posters, street banners, social media, and direct mail postcards.

Space fees are $495 for 12' x 10' spaces and $990 for 20' x 10' spaces, with corner upgrades available for an additional $100. All artwork must be original, created by the accepted artist, and for sale. White tents are required, and artists must be present during all festival hours. The application deadline is January 16, 2026, with notifications on February 16, 2026.