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Before the United States expanded beyond the Mississippi River, the land that would become Mississippi, Alabama, and Tennessee was known as the Southwest. This map shows the Old Natchez Trace passing through Choctaw and Chickasaw lands.

The Choctaw were the largest tribe along the Old Trace and share a history with it that continues to this day. Historically, when travelers left Natchez, they knew they would soon be passing the through the heart of Choctaw territory. The Choctaw were known to be excellent farmers and often provided food to early Europeans in the area. Politically, the Choctaw allied with the French and against the Chickasaw and English during the many military conflicts that arose from the 1720s until American Independence in 1783. As the United States expanded westward, pressure mounted to secure land from the Choctaw for U.S. settlement.  Choctaw lands continued to shrink through a series of land cession treaties. In 1830, the Treaty of Dancing Rabbit Creek forcibly removed most Choctaw to land west of the Mississippi River, to the present state of Oklahoma.  Some Choctaw remained in Mississippi, some returned, and today are known as the Mississippi Band of Choctaw Indians, located in Choctaw, Mississippi, near Philadelphia, approximately 25 miles east of the Parkway at Milepost 160.