The Battle of Round Mountain was the first battle in the Trail of Blood on Ice campaign for the control of Indian Territory during the American Civil War and occurred on November 19, 1861. The physical location of the battle is in dispute. Some historians believe it to be near Keystone while others contend that it is near Yale, Oklahoma
Col. Douglas H. Cooper, Confederate commander of the Indian Department, was unable to reconcile differences with Chief Opothleyahola, commander of a band of Unionist Creeks and Seminoles. Cooper set out on November 15, 1861, with about 1,400 men to either compel Opothleyahola ‘s submission or “drive him and his party from the country.” Cooper’s force rode up the Deep Fork of the Canadian River to find Chief Opothleyahola’s camp deserted. On November 19, Cooper learned from captured prisoners that part of Opothleyahola’s band was erecting a fort at the Red Fork of the Arkansas River.
Cooper’s men arrived there around 4:00 p.m. Charging cavalry discovered that Opothleyahola’s followers had recently abandoned their camp. The Confederates located and followed stragglers; the 4th Texas blundered into Opothleyahola’s warriors on the tree line at the foot of the Round Mountains. The Federal response chased the Confederate cavalry back to Cooper’s main force. Darkness prevented Cooper’s counterattack until the main enemy force was within 60 yards. After a short fight, Opothleyahola’s men set fire to the prairie grass and retreated.
The following morning, Cooper advanced on Opothleyahola’s new camp but found that the Federal forces had fled. The Confederates claimed victory because Chief Opothleyahola had left the area.
This was the first of three encounters between Opothleyahola’s Union bands and Confederate troops. The chief was forced to flee to Kansas at the end of the year.
The Confederate loss in the engagement was 1 captain and 5 men killed, 3 severely and 1 slightly wounded, and 1 missing. Opothleyahola lost about 110 killed and wounded.