Founded in 1872, and established as a trading post, Skiatook prides itself on its Pioneer Days Festival held annually in September. The Pioneer Days celebration is kicked off with a 5K run and fitness walk along the Osage Prairie Trail. A long celebrated tradition, Pioneer Days hosts a carnival with rides, live music, food tents, vendors, a parade and rodeo.
The Skiatook Bluegrass festival is an annual event promoted by the Skiatook Bluegrass Association. This event has grown every year and look forward to continuing the tradition. The festival is held at the Skiatook Festival Grounds, located behind the Skiatook Sports Complex, and the grounds have been greatly improved over the years. There is a beautiful stage, shaded seating, great food, arts/crafts vendors, children's activities, RV water and electric hookups, tent camping, great jam sessions, and friendly folks.