I'm not sure if it's due to the fact that I was in Ashland, or if its because I actually know where it is since my parents drove through Ashland last fall (hence the reason I actually know where it is) or because it seems to be the hottest thing since Miley Cyrus. Whatever it is, I've read more articles on Ashland lately than ever before (the latest issue of Sunset Magazine and Portland's Sunday paper on Father's Day).
Ashland is smack dab in the middle of the drive if you are driving from San Francisco to Portland. Conveniently enough, that's exactly the drive we were doing. On our way to Portland, we spent the night in Ashland. We enjoyed a great dinner outside on the sidewalk while watching more interesting people walk past than seems humanly possible in a small town. Our waitress just arrived in the states 4 days prior from England, she's spending the summer on the west coast working for a few weeks here and there to make money for the rest of the trip. (I did this for same thing for one summer in Ireland, only the working portion only lasted 12 days, hopefully she's a bit more successful on her money making portion of her summer abroad.) The next morning we spent a few hours shopping in all the cute stores and then had lunch by the babbling brook at a restaurant called Louie's. Louie's, by the way, offers a dog dish for the dog (clearly), however I'm sure that you are more than welcome to dish as well. Ashland seems like the perfect destination to get any unique gift under the sun. Try out Paddington Station - 3 floors of gifts galore. There's also my dream store, Flowertyme is a gift store in the front and flower shop in the back. LOVE IT!