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The Umpqua Valley AVA, Roseburg, Oregon is the oldest fine wine region in Oregon and the birthplace of Oregon Pinot Noir. As of 2011, there are over two dozen tasting rooms and that number is steadily increasing. Unlike some other wine areas, the region is very rural and uncrowed. At most wineries you can talk with the winemaker.
There are several companies which offer tours and/or guide service, so you don't have to drive. Prices vary widely.