I went to Warren Wilson College (funky place; check it out) outside of Asheville and lived there for 5 years. I haven't lived there in a long time, but I'm still connected. Around Spooks Branch Road, off Beaverdam Road, there are lots of possible neighborhoods (you'll have to do some Mapquesting to get the lay of the land there). Anything in that area will connect you to trail roads or road-ride roads.

If you can afford it, anything remotely close to the neighborhood surrounding Grove Park Inn (I'd recommend a Google Mapquest combo to figure this out) will get you to that same road/trial option.

This is just one point of view. There are many, many neighborhoods that can suit your stated needs.

I have to add that Malaprops is the best independent bookstore in the Southeast, IMHO. Have fun. It's a wonderful city. Old hippies don't die, they just reincarnate in Asheville.