Sheboss Cemetery started in the mid-1850s as a community cemetery. It is possible, but not confirmed, that it was founded around a church of Christ. There exists a photo of a church on the site, probably built around 1940 or, but there is no trace of the building remaining. The photo shows the names of the minister, J.W. Churchwell, treasurer A. H. Grey, Bible teacher Clarence Sanders, and church directors Park Boshears, Wilse Blocker and Sidney Scott. Only Sidney Scott has a marked grave in the cemetery.

Somewhere near the eventual site of the cemetery, a ‘stand' or inn for travelers known as Sheboss Place was built in the early 1800s. According to the National Park Service website, "The need for stands appeared when the US government wanted to improve the Natchez Trace into a post road to deliver mail from Nashville, TN to Natchez, MS. In 1800 most of the Natchez Trace ran through Choctaw and Chickasaw lands. A limited number of homesteads offered provisions on Chickasaw land. The stands along the Natchez Trace varied widely in size and services offered. Many stands offered very basic food along with meager accommodations. Advertisements by stand owners in Natchez newspapers focused on the travelers' diet along the Natchez Trace. The highlights included ground coffee, sugar, biscuits, bacon, and whiskey. Corn was a staple served to Natchez Trace travelers. It usually took the form of hominy, a dish prepared by soaking the corn in lye. Lucky travelers would have the option to sleep on a crude bed, but a cleared spot on the floor was what they expected. Due to cramped and dirty conditions inside the stands, many travelers chose to sleep outside on the porch or yard under the stars."

Local legend says that a widow Cranfield and her native American husband ran the stand. Her husband spoke little English, so if a traveler asked him a question, he would point to his wife and say, ‘She boss.' Thus arose the name of the stand, and the area around it.