Ranked as one of the "best small art towns," Ashland, Oregon, lives up to the honor with 30 art galleries, four theater companies and the renowned Oregon Shakespeare Festival. The Festival draws more than 350,000 visitors a year and procudes 11 plays between February and October: Five are Shakespearean works, with the rest divided among other classics and the works of modern playwrights.

The creative focus extends to food, too. Ashland, a town of about 20,000 residents located 285 mi/460 km south of Portland, boasts 100 restaurants. Each spring, a highlight of the local calendar is the Taste of Ashland, a combined effort of local wineries, restaurants, fruit growers and galleries.

Because it sits in a fertile fruit-growing region, Ashland is a good place to pick your own cherries, apricots, nectarines and peaches. Try the 50-acre/20-hectare Valley View Orchard. Wineries abound, too—most schedule tours and tastings.

Take a self-guided tour to see a few of the town's 500 historic homes, churches and buildings. Many of the old homes have been converted into bed-and-breakfasts.

Skiing at nearby Mount Ashland is a popular draw in the winter. At least half of the trails, which offer good views of the Rogue River National Forest, are geared to experts.

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