Chisholm used this trail to supply his trading posts among the Native American tribes in Indian Territory, what is now western Oklahoma.
Chisholm served as an interpreter for the Republic of Texas and the United States government in treaty-making with Native American tribes.
Chisholm's father, Ignatius, was of Scottish descent and probably also a trader, and his mother Martha (née Rogers) was a Cherokee from the region of Great Hiwassee.
In 1826, Chisholm became involved in working for a gold-seeking party, who blazed a trail and explored the region to present-day Wichita, Kansas.
In 1834, Chisholm was a member of the Dodge-Leavenworth Expedition, who first contacted the southern Plains Indians on behalf of the United States federal government.
At the war's end, Chisholm settled permanently near present-day Kingfisher, Oklahoma, and again began to trade into Indian Territory.