Oh, dude, no question.

ASHLAND, OREGON!

My brother lives there, going to college. It's a college town, (you know, centering around a college) and everyone is either a hippy or a hot chick. The whole place is on one big hill, so you can live at the top, and just coast a bike all the way down to the BEST skatepark I've ever been to at the bottom. There's a great selection of stores, freaking everything. There's like 5 music stores, a bunch of nightclubs and cafes, some of the best food, and this building that looks like the Alamo.

Oh, don't forget snowboarding, rockclimbing, skateboarding, and whitewater rafting all within 20 miles.

Seriously, best town ever.