You'll get some folks on this website who will try to help you however they can, but the website purpose is more in the nature of backcountry hiking and camping rather than rambling across the country.

You might want to take a look at this website: www.theworldwalker.com

Back in the 80's he walked "around the world" and wrote a couple of books about it; I think he's done some additional trips since. He blended some camping with other types of travel, hitting cities and rural areas (though not really much time in backcountry settings.)

I met him once, in the late 80's or early 90's, when I hired him to speak at the local high school. He impressed me as a very approachable person, so you might try contacting him through his website. I know he's busy, but if you could establish a connection, he would be a marvelous source of information for the kind of trip you're toying with.