Scot-Cherokee trader Jesse Chisholm first marked the famous Chisholm Trail in 1864 for his wagons. It started at the Little and Big Arkansas Rivers and went to Jesse Chisholm's trading post, southwest of present day Oklahoma City.

​

Jesse Chisholm used the trail to trade with the U.S. Army and Native American tribes (Indians) from his trading post at the present site of the Twin Lakes Shopping Center in Wichita to his southern trading post in Indian Territories. The Wichita Indians used the Chisholm Trail when they moved from their native territory to the mouth of the Little Arkansas and also when they returned in 1868.

​

Joseph G. McCoy, a cattle buyer from Illinois, was instrumental in extending the Chisholm Trail from present day Wichita to Abilene, Kansas, to promote and establish cattle market for thousands of longhorn cattle from Texas. In 1867, McCoy built stockyards that he advertised throughout Texas. Approximately 35,000 cattle followed the Chisholm Trail during the first season to Abilene in 1867. Through Joseph McCoy's promotional and entrepreneurial efforts Abilene became a prosperous and famous cattletown from 1867 to 1870.

In the five years from 1867 to 1872, more than three million head of cattle were driven up the Chisholm Trail from Texas to Abilene.

By 1870 thousands of Texas longhorn cattle were being driven over the Chisholm Trail to the Union Pacific (later the Kansas Pacific) Railroad shipping center at Abilene. By 1871 as many as 5,000 cowboys were often paid off during a single day. Abilene became known as a rough town in the Old West.