This past weekend I got a chance to hear William Least Heat-Moon at Portland's Wordstock Festival. In the late 1970s he hit the road after a particularly bad day in which he got fired from his job and split from his wife. His three month road trip became the best-selling book, Blue Highways. He stayed away from major highways, sticking instead to the back roads which are usually indicated by the blue lines on the map, (hence the title).
He's also documented an Un-Road Trip of his own in River-Horse, in which he crossed the entire United States, using its waterways, in his 22-foot boat. Most recently, he's published Roads To Quoz about a road trip he took with his wife, concentrating on visiting small towns in America.
He's spent a lot of time both traveling alone and with others, and he had a few recommendations. He warned that, "the greatest danger of traveling alone is desolation." On the upside, when he's traveled alone, it's easier to find time to document everything. You may feel isolated and crazy without others, but you'll be able to write and photograph without distraction. On the flip-side, it can be tough approaching strangers when alone, because who's to say you're not crazy. If you're with someone else, you've got at least one guy to vouch for you...
I'll definitely keep all that in mind when I hit the un-road.