Southern Oregon begins where the verdant lowlands of the Willamette Valley give way to a complex collision of mountains, rivers, and ravines. The intricate geography of the "Land of Umpqua," as the area around Roseburg is somewhat romantically known, signals that this is territory distinct from neighboring regions to the north, east, and west.

Wild rivers—the Rogue and the Umpqua are legendary for fishing and boating—and twisting mountain roads venture through the landscape that saw Oregon's most violent Indian wars and became the territory of a self-reliant breed. "Don't-Tread-on-Me" southern Oregonians see themselves as markedly different from fellow citizens of the Pacific Wonderland. In fact, several early-20th-century attempts to secede from Oregon (in combination with northern California) and proclaim a "state of Jefferson" survive in local folklore and culture. That being said, Ashland and parts of the surrounding area have steadily become more progressive and urbane in recent decades, as wineries, art galleries, and farm-to-table restaurants continue to proliferate. The mix of folks from all different political, social, and stylistic bents is a big part of what makes southern Oregon so interesting—and appealing.

Some locals describe this sun-kissed, sometimes surprisingly hot landscape as Mediterranean; others refer to it as Oregon's banana belt. It's a climate built for slow-paced pursuits and a leisurely outlook on life, not to mention agriculture—the region's orchards, farms, and increasingly acclaimed vineyards have lately helped give southern Oregon cachet among food and wine aficionados. The restaurant scene has grown partly thanks to a pair of big cultural draws, Ashland's Oregon Shakespeare Festival and Jacksonville's open-air, picnic-friendly Britt Festivals concert series.

Roseburg, Medford, and Klamath Falls are also all popular bases for visiting iconic Crater Lake National Park which lies at the region's eastern edge, about two hours away by car. Formed nearly 8,000 years ago by the cataclysmic eruption of Mt. Mazama, this stunningly clear-blue lake is North America's deepest.