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About Winona, MS 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, development shifted to what became Winona and bypassed Middleton. Pre-1900s [ edit ] 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.
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