As many of you probably know, the Yellowstone Trail was an early transcontinental highway during Model T days (1912-1930).
Although not an old song (it is from 1910), there is a song about the Yellowstone Trail you can listen to at: http://www.scoreexchange.com/scores/117564.html
More info about the Yellowstone Trail can be found at:: http://www.yellowstonetrail.org/index.htm and http://yellowstonetrail.tumblr.com/
John, it goes right through Renville County, Minnesota, where I live. I have been interested in the road for years. You must know John and Alice Ridge.
Lance & John, it goes right through the middle of my ranch at Westmore, Montana. There is one of the tapered yellow markers still at the corner where the road used to turn to the east rather than crossing the Milwaukee tracks. Roberta Willman painted it a few years ago, it still had traces of yellow paint on it.
Please forgive the wrong date for the song in my posting above. I meant to write that the song was from 2010! I guess that sometimes my brain gets stuck in the 1900s.
If you go to the page for the song, click on the MP3 icon to listen to it.
I don't know John and Alice Ridge personally, but I am just now reading their very interesting book titled Introducing The Yellowstone Trail, which I purchased from the Yellowstone Trail website. It is only about 90 pages, but is a good overview of the Yellowstone Trail and its history.