The Winona post office was opened in 1852, two years before it became the county seat of Winona County. It was previously part of Fillmore county, which was split off from Wabashaw county a year or two before. Wabashaw county was one of the original nine counties in the Minnesota territory.
Edit: I believe the machine cancel is a Columbia Postal Machine cancel. (I picked one up much like it this weekend).
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