It was located about 1 mi (1.6 km) east of the Chickasawhay River, and south of "Three-Chopped Way", a pioneer road completed in 1807 connecting Georgia and the Carolinas, via St. Stephens, Alabama, with Natchez in eastern Mississippi.

[6] When the Mobile and Ohio Railroad was completed in the 1850s, the track passed a distance north of the town, and a station was erected there.

[2]: 985 Another may have been the 1830 Treaty of Dancing Rabbit Creek which forced the removal of the Choctaw people from Mississippi and opened up large areas to the north which drew off the populations of Wayne and Lawrence Counties.

[6] Still another reason may have been offered by a writer in 1894 who stated about Winchester: There was no church in the town until forty years after it was settled.

It appears that the morals of the people who lived in the town were averse to churches... liquor was sold openly on the Sabbath and [there was] much drunkenness on that day.

A historic marker is located along U.S. Route 45 at Winchester Cross Road which reads: "About one mile to the West.