Winona is a city in Montgomery County, Mississippi, United States. 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 were constructed here. History Middleton 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. Winona 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. The railroad attracted business, which developed around the station as Moore sold off some property. Winona was incorporated as a town on May 2, 1861. Settlers were attracted because of the railroad access, and Winona became a busy trading town. Captain William Witty, an early settler from North Carolina, was for years a leading Winona merchant and established the first bank in the county. Other names of early settlers were: Curtis, Burton, Palmer, Spivey, Townsend, Hart, Turner and Campbell. The early businesses were mainly grocery stores. In 1871, the Reconstruction-era state legislature organized Montgomery County from portions of Carroll and other counties, and Winona was designated as its county seat. A yellow fever epidemic struck the area in 1878, and resulted in the deaths of many residents. Some people left the town in an effort to outrun the epidemic, which spread with river passengers throughout the waterways of the Mississippi Delta and nearby counties. In April 1888, a great fire destroyed almost the entire business section of the town. Forty of the 50 businesses burned. In 1890 the state passed a new constitution that effectively disenfranchised most blacks, excluding them from the political system. In addition, Jim Crow laws were passed imposing second-class status on them, a condition enforced by whites for decades. 20th century to present Following their service in World War II, many African Americans began to press to regain their