285 miles S of Portland, 50 miles W of Klamath Falls, 350 miles N of San Francisco

With classy cocktail bars and upscale restaurants, live jazz in the clubs and cafes, lots of art galleries, and day spas that take advantage of Ashland's famed Lithia Springs mineral waters, Ashland has become the most cosmopolitan community in southern Oregon. Sure, this is still a small town 5 to 6 hours by car from San Francisco or Portland, but more than half a century of staging Shakespeare plays has turned Ashland into Oregon's preeminent arts community, which in turn has attracted the city's diverse population. Because this is one of the best little arts towns in America, come prepared to fall in love.

Ashland's rise to stardom began on a midsummer's night back in 1935. In a small Ashland theater built as part of the Chautauqua movement, Angus Bowmer, an English professor at what is now Southern Oregon University, staged a performance of Shakespeare's As You Like It. Despite the hard times that the Great Depression had brought to this quiet mill town in the rugged Siskiyou Mountains, the show was a success. Although the Depression had dashed any hopes local businessman Jesse Winburne had of turning Ashland into a mineral-springs resort, the hard times did not hit until after he had built beautiful Lithia Park. Luckily, each man's love's labor was not lost, and today their legacies have turned the town into one of Oregon's most popular destinations.

The Oregon Shakespeare Festival, born of Bowmer's admiration for the Bard, has become a world-class repertory festival that stretches across 9 months, and although Ashland never became a mineral-springs resort, Lithia Park, through which still flow the clear waters of Winburne's dreams, has become the town's centerpiece. When not wandering the park's pathways, you can go wine tasting or check out one of the state's best shopping districts. Head farther afield and you can hike and bike in the mountains and forests that surround Ashland. In other words, there's plenty to do when the curtains go down and the stages are dark.