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I was going to try it last year by motorcycle, but never did. After some preliminary research, it seems only parts of Route 66 still exist, and you need to plan out your stops, as much of the route is not very populated. I would suggest checking online for more information...one site is http://www.historic66.com/ but there are others. Should be a nifty trip!
Much of the America's road has been either abandoned, or overbuilt with highways.
From our experiences - Oklahoma, NM and parts of AZ have the best of the best still existing.
The web site http://www.historic66.com/ is a good place to start your analysis - also Goggle and you'll find a lot of information not covered by this site.
Take a GOOD camera - every year there is less and less of the "road" remaining - pictures of the trip will be a keep sake for many years to come.
Has anyone ever driven Route 66 from one end to the other? What was it like?
In 1962 a friend of mine bought a 62 327-340 black on Red convertible and he and I drove from Louisiana to California using Interstate 20 and I-10 taking the southern route. We came back through Yosemite over to Las Vegas, drove south of Las Vegas and picked up Route 66 in Kingman, AZ. We drove on Route 66 all the way to Amarillo, Texas before having to turn southeast back to Louisiana.
I have many stories to tell and memories that money can't buy. Wish all you guys could have had the same opportunity.
As mentioned, most of it is gone, and most of what is left is in miserable condition. May I suggest a few alternatives?
The Lincoln Highway, America's first coast-to-coast highway. This is still there, and not freeway. Good stuff, especially US50 through Nevada, "The Loneliest Road in America".
The Lewis & Clark Trail. This is not a single highway, but a series of roads that run on or parallel to Lewis & Clark's route. A lot of these are killer roads, and there are great roadside markers and museums.
The Million-Dollar Highway in Colorado. Not long, but truly amazing.