Based on arrowheads found on Wessyngton Plantation, Native Americans lived in the area thousands of years ago. Arrowheads and other Native American artifacts have been found at Wessyngton by farmers plowing the fields for many years.
During the Cherokee removal known as the Trail of Tears during the 1830s, hundreds of Native Americans passed through Robertson County, Tennessee. Descendants of the Washington family and African Americans who lived at Wessyngton told their descendants that Native Americans came to the Wessyngton mansion to get food and water enroute to Port Royal. They were marched from Port Royal to Hopkinsville, Kentucky where they spent the winter of 1838-39. From Hopkinsville they were forced on to the reservations in Oklahoma.