Winona, Mississippi got its start when Colonel O.J. Moore arrived from Virginia in 1848 and established a plantation in the area. When the Mississippi Central Railroad came through in 1860, they bought a part of Moore’s land and ran tracks which would eventually become part of the Illinois Central Line from Chicago to New Orleans. Moore sold some more land around the station and a few businesses sprung up to serve the rail travelers. When the town was incorporated in 1861, they chose the name Winona, which is apparently the name an Indian Chief would give his first-born daughter. After the Civil War, Montgomery County was organized, and Winona was chosen as the county seat. While the trains no longer pass through Winona, it still sits at the crossroads of highways 51 and 82 and is just a short distance from Interstate 55.It also rests right between the Delta and the Hills regions of the state. Winona has often been called the “Crossroads of North Mississippi”, but I’ve also seen it called the “Art and Soul of Mississippi”, a nickname which I think I prefer. This Norman Rockwellesque town of about 5000 is definitely full of charm and worth a detour from the highway. I wasn’t there long, but I definitely enjoyed my stay in tiny Winona, Mississippi. I hope you enjoy these photos from my visit.
