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Winona is a city in Montgomery County, Mississippi, United States. The population was 5,482 at the 2000 census. It is the county seat of Montgomery County. Winona is known in the local area as "The Crossroads of North Mississippi" due to its central location at the intersection of U.S. Interstate 55 and U.S. Highways 51 and 82.
Middleton, Mississippi was a town that was located west of Winona's current geographical position. It is sometimes considered the predecessor to the current town, Winona.
Born as a result of the railroad being built here instead of at Middleton to the west in 1860, Winona was originally a part of Carroll County and was incorporated as a town on May 2, 1861. The first settler of the town was Colonel O.J. Moore, who arrived from Virginia in 1848. What is now the business part of town was then a cultivated field on Colonel Moore's property. The railroad passed through his property and the railway station was placed near his plantation home. An influx of settlers started after the location of the railroad and Winona became a busy town.