About twenty years ago, while day-hiking in the southern part of the Peak District, I got talking to a guy who was walking the same section of road as me. He was pretty shabbily dressed and his shoes were worn-out, and he said he was walking from (I think) Birmingham to Carlisle to stay with his brother because he had no money and nowhere to live. He told me he was keeping away from towns and sleeping in forests and barns. All his possessions were stuffed into the pockets of his coat. We walked a couple of miles together and he seemed like a nice guy.

Not exactly a "gentleman of the road" with a spotted-hanky-bundle on a stick, but the nearest I've seen to an archetypal tramp. I hope he made it.