The Cleveland Apple Festival is always held the 3rd weekend in October. It is a family event in downtown Cleveland, Tn. This annual festival offers a juried art and craft show, live bluegrass music, food booths, pony rides, hayrides, entertainment, recipe contest, apple pie eating contest, Little Miss Apple Blossom contest, all children's activities in the Trailhead Bicycle Kid's Zone are free to children 12 and under including the pony rides! Fun for the whole family!