Winona is a city in Montgomery County, Mississippi. The population was 5,043 at the 2010 census. It is the county seat of Montgomery County. Winona is known in the local area as "The Crossroads of North Mississippi"; the intersection of U.S. Interstate 55 and U.S. Highways 51 and 82 was constructed here.
Middleton, Mississippi was a town that developed in the 19th century two miles west of Winona's site. Some locals consider it the predecessor to Winona. After the railroad was built to the east of Middleton, development shifted to what became Winona, bypassing Middleton.
The first European-American settler in the area, which was originally part of Carroll County, was Colonel O.J. Moore, who arrived from Virginia in 1848. He agreed to the railroad being constructed through his property, and a station was built in 1860 near his plantation home.
As a result of the railroad line and station being built here rather than Middleton, Winona was founded and began to grow.