Roughly defined as the area from the California state line in the south to a little way north of Roseburg, southern Oregon is a mountainous region that has far more in common with northern California than it has with the rest of Oregon. The landscape is much drier than in northwestern Oregon, and dominating the region are the Siskiyou Mountains, a jumble of rugged peaks and rare plants that link the Cascades and the Coast Range.
It was gold that first brought European settlers to this area, and it was timber that kept them here. The gold is all played out now, but the legacy of the gold-rush days, when stagecoaches traveled the rough road between Sacramento and Portland, can be seen in picturesque towns such as Jacksonville and Oakland.
Although southern Oregon is a long drive from the nearest metropolitan areas, it is relatively easy to plan a multiday trip from San Francisco or Portland. From Ashland, the southernmost city in the region, it's roughly a 6-hour drive to either Portland or San Francisco.
Ashland is the region's most popular destination and is renowned for its Oregon Shakespeare Festival, which attracts tens of thousands of theatergoers annually. The festival, which now stretches through most of the year, has turned what was once a sleepy mill town into a facsimile of Tudor England. Not to be outdone, the Britt Festivals in the nearby historic town of Jacksonville offer summer performances by internationally recognized musicians and dance companies.
However, it isn't just the Bard that attracts visitors to this region. The rugged beauty of the Siskiyous and the wild waters of the Rogue and Umpqua rivers are big draws as well, with rafting and jet-boat tours providing options for getting out on the water. In recent years, this region has also seen a proliferation of wineries in both the Umpqua Valley west of Roseburg and the Applegate Valley west of Jacksonville. Because this region is so much warmer than the Willamette Valley wine country, it grows a wide variety of Bordeaux, Rhone, Italian, and Spanish varieties of grapes. So even if you've got a trunk full of pinot noir, you might want to do a little more wine touring in this region so you can pick up some cabernet sauvignon or tempranillo.