Checotah began as a settlement of Creek Indians in the 1830's following their removal from Alabama. History in the vicinity is related to trials and tribulations of the people during the War between the States.
One of the most significant battles in this area was the battle of "Honey Springs" or "Elk Creek" which occurred on July 17, 1863. The battle site is located approximately four and one half miles northeast of Checotah. The fight was between forces of the Confederates and Federals. Factions of the Creek tribe fought with each respective army.
Following the Civil War, re-establishment of tribal boundaries greatly reduced the Creek Nation land area.
Ensuing years found railroads building across the countryside throughout Indian Territory. Railroads provided transportation for cattle and agricultural products to major markets and distribution centers. During this time Checotah came into being by a peculiar set of circumstances.
Principal cheif of the Creeks at the time was Samuel Checote who had served the Confederacy as a lietenant colonel in the First Creek Regiment. He was vehemently opposed by another faction within the tribe. Folowers of Sand Ok-ta-ha contended that he was defrauded out of office of chief in the election of 1867. During "Sand's Rebellion," the Missouri-Kansas-Texas Railroad(MK&T) was constructing a line through present day Checotah, a part of the Creek Nation. A switch station along this line was named for each chief. Therefore, the original townsite of Checotah was named for Sam Checote and a rail station six miles north was named Ok-ta-ha.
The eventual extension of rail facilities in the area helped commerce to flourish. Large scale cattle ranches and cotton farms were abundant. Establishment of a post office in the community was made on June 17, 1886. A four-bloc area in downtown Checotah is now on the National Historical Register.