Ashland

As you walk Ashland's hilly streets, it seems like every house is a restored Victorian or Craftsman operating as an upscale B&B, though that's not nearly all there is to this town: the Oregon Shakespeare Festival attracts thousands of theater lovers to the Rogue Valley every year, from late February to early November (though tourists don't start showing up en masse until June). That influx means that Ashland is more geared toward the arts, more eccentric, and more expensive than its size (about 21,000 people) might suggest. The mix of well-heeled theater tourists, bohemian students from Southern Oregon University, and dramatic show folk imbues the town with some one-of-a-kind cultural frissons. The stage isn't the only show in town—skiing at Mt. Ashland and the town's reputation as a secluded getaway and growing culinary destination keep things hopping year-round.