In 2009, I took a beat-up 1973 Mercury Marquis on a massive, old school (no GPS, minimal freeway use, no hotels) road trip around the western US. I've finally put together a travelogue about it, sort of a poor man's Ken Burns of the trip. I soundtracked it with a pretty wide selection of jazz, big band, blues, bluegrass, some classic rock, and a little light disco. It's the most interesting thing I've ever done, told about as well as I'll ever be able to tell it. I know I'm not terrifically active on the forums, but I do lurk a great deal, and enjoy The Escapist. If you've got the time for a classic American travelogue, I have one for you here:
http://www.youtube.com/watch?v=3Mq8QzPog6E