Here is one site that gives a good quick history of "The Main Street of America". Here's an excellent one from the National Park Service. And there are plenty of others.
Here's one: Ghost Towns of Route 66. Once the interstates came through, they sucked what lifeblood remained from the small western towns.
How about Route 66 in postcards?
One website will give you a Route 66 slideshow.
Route 66 even has a song written about it. You can watch it performed by Nat King Cole here, or watch the Rolling Stones cover it here.
And this I did not know until just now: it is a cultural treasure akin the ruins of Pompei, the Andean city of Machu Pichu, as judged by the World Monuments Watch, which focuses global attention on cultural heritage sites around the world in dire need of preservation.
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