Ashland is home to the Oregon Shakespeare Festival which runs from late February to November as well as other arts groups. The Ashland Food Coop is not only a great organic food store but their buffet has a large selection of salads, sides and main dishes. I ate there 4 or 5 nights a week. Doesn't pay to cook for one with the Coop available.
I parked at Wellsprings RV park and spa about 1.5 miles from downtown Ashland. Wellsprings hosted festivals and concerts which added to the artsy flavor of the area.
Watch the videos shot at Wellsprings.