About 10 years ago there was a PBS series called "Great Drives" that documented five great American highways. The really interesting segment was Levon Helm driving Highway 61 from Memphis to New Orleans in a 58 Buick, retracing his roots and a lot of Blues history. I did a little checking on the web but didn't find the video available anywhere but there is a little info here:
http://theband.hiof.no/videos/great_drives.html
and here:
http://www.imdb.com/title/tt0283733/plotsummary