An endearing guy without much common sense, Vernon Praiseworthy (Tim Conway) is in line to inherit a huge sum of money from his uncle, Choo-Choo Trayne (Will Geer), a hobo who became a billionaire. In order to get the money, though, Vernon has to experience the hobo way of the life. While on his extended railway adventure, Vernon travels with a bright dog and gets into numerous mishaps. Not surprisingly, the mutt seems to have a better handle on things than his human companion.