Woodstock Art Fair on the Square

Start: Saturday, October 3, 2026 10:00AM
End: Sunday, October 4, 2026 5:00PM

Woodstock Art Fair on the Square is filling Downtown Woodstock Square with 75 original artists on October 3-4! Start your family or friend’s day downtown with coffee and breakfast, then soak in the creativity of the fest! Make your masterpiece at our live painting class, or plan a creative stop in the Kids Art Zone. Break for lunch and enjoy a cold beer, lemonade and delicious snacks at the fest. Be sure to look for Kid Friendly Art Tent and Live Art Demo signs to get interactive with the artists. Many of Woodstock’s great restaurants, cafes and retail stores are open all weekend. Enter to win a $100 Art Fest Gift Card to spend at the fest!