Located on the Osage River, the land that became the town of Osceola was inhabited by the tribe of Osage Native Americans, also known as NiuKonska, Native Americans who gave the river its name.

Two treaties, in 1808 and 1825, signed by the Osage and the U.S. government gave up all the tribe's land in Missouri.

With the way cleared for non-native settlers, more people began to arrive in the St. Clair County area in the mid-1830s.

The town of 2,077 people was plundered and burned to the ground, 200 slaves were freed and nine local citizens were court-martialed and executed.

[6] The event inspired the 1976 Clint Eastwood film The Outlaw Josey Wales.

[7] The Osceola Public School Building was added to the National Register of Historic Places in 1999.

This event includes the street dance, food vendors, and the Rodeo Daze Parade.

The annual street dance is held on the Thursday before Labor Day.

[16] Osceola is the birthplace of Rooster Cogburn in Charles Portis's 1968 novel True Grit.

[17] The pillaging of Osceola by Kansas Jayhawkers and Red Legs is thought to have provided Cogburn's motive for taking part in William Quantrill's infamous sack of Lawrence, Kansas which serves as a biographical background to the story.