This pretty city is the cultural center of Southern Oregon thanks to its internationally renowned Oregon Shakespeare Festival (OSF), which runs for nine months of the year and attracts hundreds of thousands of theatergoers from all over the world. The festival is so popular that it's Ashland's main attraction, packing it out in summer and bringing in steady cash flows for the town's many fancy hotels, upscale B&Bs and fine restaurants.
Even without the OSF, however, Ashland is still a pleasant place whose trendy downtown streets buzz with well-heeled shoppers and youthful bohemians. In late fall and early winter – those few months when the festival doesn't run – folks come to ski at nearby Mt Ashland. And wine-lovers, take note: the area has several good wineries worth seeking out.