You will find tons of cute little shops downtown, and, no sales tax. Quite a stunner from someone used to paying almost 10% back home.
Some of the nicest people I've EVER come across live here. Cars, even humongous four-wheel drives driven by heavily tattooed grunge-ish looking youth, will stop even before you set foot into the intersection.
Downtown Ashland is just bursting with tons of awesome restaurants and smaller cafes. The only downside is that their coffee is way way too weak here for my taste. (Although on our way out I happened across Noble Coffee Roasting--they roast on site and it is stellar brew!)
Lithia Park is just beautiful, sprawling woodsy landscape decked with Japanese Maples and the most laid back Mallard ducks I've ever seen. Eerily quiet but so relaxing. My daughter keeps asking if anyone else is staying at the hotel.
And Shakespeare. I could stay here a very long time.