Middleton: The Town the Railroad Erased

Middleton in Montgomery County, Mississippi, was once a thriving commercial and educational center , the kind of town that could aspire to become a county seat. The first settler, Irelton DeVane, built a log trading post here around seventeen ninety and did business with the Choctaw, whose territory this was. Other families from Kentucky and the Southeast followed in the eighteen twenties and thirties, and Middleton grew into a genuine village with churches and schools.

In eighteen fifty-nine the Mississippi Central Railway , later absorbed into the Illinois Central , laid its tracks through the area. The railroad bypassed Middleton. It passed instead through the nearby community that became Winona. Businesses and residents followed the rails, as they always did, and Middleton emptied out. The town that had seemed destined for permanence vanished within a generation.

All that survives today is Middleton Cemetery, restored by the Winona Lions Club in nineteen ninety-two , a scatter of graves marking the place where a town once stood, erased by a surveyor's decision about where to run the tracks.