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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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11/29 Coming to The area
Spring Thaw Mountain Bike Festival Ashland OR May18-19 The Spring Thaw is Oregon's largest mountain bike event.
Mt. Pisgah Arboretum Wildflower and Music Festival Eugene OR May19 A day of wildflowers, music, food, crafts, and microscopes!
Rhododendron Days Florence OR May17-19 The annual celebration of the blooming of rhododendrons along the central Oregon Coast.
Azalea Festival Brookings OR May24-26 The community-wide festival includes a parade, street fair, art show, car show, flower & quilt shows, breakfasts and BBQ's