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.

Oregon Wine Country Tours  http://www.oregonwinecountrytours.com/ 

(The only local wine tour company)

Sunshine Limo Wine Tours  http://www.sunshinelimoservice.com/wi...

Roseburg Wine/Private Tour Limo Services   http://www.limos.com/geo/United-State... 

(When  searcing  this link for a wine tour in Roseburg the result is: "Sorry,  could not match a vehicle to your request.")

Grand Cru Wine Tours http://www.grandcruwinetours.com/  (Leaves from Eugene)

If you would prefer a self guided tour, this website includes a list and map of Umqua Valley Wineries...  http://www.visitroseburg.com/wineries...

While in Roseburg, enjoy your visit to the local wineries.