Avoid Medford. It's just outside of Ashland. Bleehhhhh! ::hungover::
Although I did meet some cool other folks there that were also trying to get the fuck out of Medford, and got picked up by one of my favorite rides ever, so I guess really wherever you are... there can be good shit too.
Speaking of that area, I honestly wasn't a fan of Ashland either but most people love it. (Really I think I disliked it because it was like a weird Twilight Zone identical -- but off -- version of a place I used to live and hated). If you are trying to get weed, that would be a good place to look for sure, though. "Hippies" galore.