Winchester is located just north of Roseburg, along Interstate 5 and the North Umpqua River. The community of Winchester, which was founded by the Umpqua exploring expedition of San Francisco in 1850, was laid out by Addison R. Flint. For a number of years it was the largest settlement in the Umpqua Valley. Winchester post office was established November 3, 1851, with A. R. Flint as the town's first postmaster. There is also a Winchester, Virginia.
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