I am from Gypsum which is really pretty close to Aspen. We have some great trails and we also have a friend in Basalt who has some trails. He is from Illinois also. Aspen also has Taylor pass and some good rides. If you want a guide call us and we can hook up. Send me an e-mail.
Ben and Nicole
I've ridden from Crested Butte into Aspen and back before. You do have to go over Taylor Pass. Every type of terrain was ridden to get there. If you can find someone to direct you, I would highly recommend riding in Crested Butte for lunch and back to Aspen.