This former gold-prospecting town is the oldest settlement in Southern Oregon and a National Historic Landmark. Small and endearing, the town's main drag – California St – is like a step back in time, lined with well-preserved brick-and-wood buildings dating from the 1880s. Today folks come to stroll around downtown and enjoy the old-time atmosphere while exploring the many boutiques and galleries. Although summertime is great, Jacksonville has a certain magic in winter, when the crowds are lighter and the old-fashioned 'Victorian Christmas' holiday celebrations take hold.
Don't miss the Britt Festival, a world-class series of concerts that runs all summer long.
Oenophiles who think of Oregon as strictly Pinot Noir territory should investigate the Applegate Valley wine trail, where an increasingly well-regarded group of wineries is producing excellent non-Pinot varietals, like Tempranillo and Cabernet Franc.