I would combine SadieKate's and Surlygirl's ideas. I've driven cross-country a couple of times and had a great time. I'd love to do it again. Didn't see nearly everything there is to see.

I'd suggest a more Southern route to get across the Rockies, since high mountain passes may be closed during winter and to avoid nasty winter storms, too. You'll probably have to get chains for the truck for high mountain passes, too. Not that I have lots of experience......

You are more than welcome to use my place as a stop along the way. I've had numerous people from bikejournal put me up so I can "pass it on."