Winter Park Sidewalk Art Festival

Masterpieces of fine art draw fans and local artists alike to the 67th annual Winter Park Sidewalk Art Festival. From March 20 to March 22, 2026, enthusiasts can tour a variety of exhibits featuring paintings, jewelry, 3D art, clay art, glass art, and photography in downtown Winter Park. Local artists compete for cash prizes, and aspiring young artists can show off their skills at the Children's Workshop. Refresh in beautiful Florida weather with delicious local dishes and groove to the tunes of live music.