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I'm in the early stages of planning a trip on route 66. I never owned a Garmin before. Can you install/upload a map of route 66 in any Garmin? Is there such a thing?
The short answer is yes. But you have to be aware that portions of Route 66 no longer exist, so you'll need to use other roads, most often the nearby interstate that killed the old road in the first place.
Do a google search for Route 66 via GPS. That should get you the .gpx files that you might need to upload to your GPS, depending on what maps it already has installed.
If you are using a Garmin device, you can make the mother road easier to find by turning off the GPS's normal inclination to use the shortest or fastest route, which is almost always the interstate.
I would also get a good set of paper maps for all the states you plan to travel through, because many times a paper map will show you things that a GPS won't. A partner who can serve as occasional navigator is another good idea for a trip like this.
We did this trip 10 years ago on motorcycles, and it was a lot of fun. Started in Chicago, ended up at the Santa Monica pier.
If you know exactly what roads you want to take, and aren't really trying to get 'from here to there', then I'd suggest using Google maps to plan the exact trip you want to take. Once you manually move the route to your preferred roads you can sometimes send that route to a phone or Nav device, but you can always email a link with your preferences. Send that link to yourself, or save it as a favorite on a laptop, then just check it every morning before setting out on your adventure.