Ashland's small, very pretty... location of Southern Oregon University and a gigantic annual Shakespeare festival, which keep it from being too much of a redneck town. Never visited for more than a day or two at a time, but everyone I know who's lived there has loved it.

Portland is Portland. It's a good place. If you want to work up here after you finish UBI, though, you'd better start making phone calls as soon as you get to Ashland...