Trail of Blood on Ice The Trail of Blood on Ice was a campaign in the American Civil War in which pro - Union Native Americans led by Upper Creek Chief Opothleyahola fought their way north from Oklahoma ( then under Confederate control ) to Kansas , while facing attacks from Confederate forces under Col . Douglas H . Cooper . Background . With the secession of eleven Southern states in 1861 , both the Union ( American Civil War ) and the Confederate States of America vied for control of the Indian Territory . Old tribal rivalries were renewed , with some aligning with the North and others with the South . When a Confederate force under Col . Douglas H . Cooper attacked Unionist tribes in the Indian Territory , Upper Creek Chief Opothleyahola resisted and led Indians loyal to the Union from McIntosh County , Oklahoma north to Fort Row , Kansas . Loyal Indian warriors fought Cooper in a series of battles in the winter of 1861 – 62 that led to the withdrawal of the Union sympathizers to Kansas in a bitter trek known as the " Trail of Blood on Ice . " Battle of Round Mountain . The first engagement , the Battle of Round Mountain occurred on November 19 , 1861 near the Red Fork of the Arkansas River . The actual location is in dispute as some historians believe it to be near Keystone , while others believe it to be near Yale , Oklahoma . 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 . Battle of Chusto - Talasah . The second engagement , the Battle of Chusto - Talasah also known as " Caving Banks , " was fought on December 9 , 1861 near Sperry , Oklahoma . For almost four hours , Cooper attacked and attempted to outflank the Federals , finally driving them east across Bird Creek just before dark . Cooper camped there overnight but did not pursue the Federals because he was short of ammunition . The Confederates claimed victory . Chief Opothleyahola and his band moved off in search of security elsewhere . Their loss was estimated by Cooper as 500 ( some accounts suggest 412 ) . Confederate casualties were 15 killed and 37 wounded . Battle of Chustenahlah . The third and final engagement , the Battle of Chustenahlah occurred on December 26 , 1861 near Skiatook , Oklahoma . Colonel James M . McIntosh and Cooper , planned a combined attack with each of their columns moving on the camp from different directions . McIntosh left Fort Gibson on December 22 , with 1 , 380 men . On December 25 , he was informed that Cooper ’ s force could not join him for a while , but he decided to attack the next day , despite being outnumbered and severe cold weather conditions . McIntosh assaulted the camp at noon . The 1 , 700 pro - Union defenders were secluded in the underbrush along the slope of a rugged hill . McIntosh devised a plan to converge on the crest , with the South Kansas - Texas Cavalry ( also known as the 3rd Texas ) ordered to charge directly up the steep bluff on foot . The 11th Texas advanced to their left using a defile for concealment , while the 6th Texas circled to the right . As the Confederate attack progressed , the Native Americans began to fall back , taking cover for a while and then moving back . The retreat became a rout as the Federals reached their camp . The Indians attempted to make a stand there but were forced away again by 4 : 00 p . m . The survivors fled ; many went all the way to Kansas where they found loyal Unionists . Three hundred Cherokees under Col . Stand Watie intercepted the fleeing Creeks and Seminoles , killing 15 of them . Sonuk Mikko ' s band of Seminole Indians covered the rear after the battle against Cherokee chief Stand Watie . Aftermath . They eventually settled near Fort Belmont , where a number of his Seminoles perished of exposure and starvation during the winter . Chief Opothleyahola ’ s band mounted no further resistance , and nearly 2 , 000 of them died on or shortly after the trek to Fort Row , Kansas , mostly due to exposure and disease .