There's a new role-playing game set in the Depression where you play hobos riding the rail and — that's right — chalking the presence of sherriffs and soft touches. The site includes a sample from the rulebook with a bunch of hobo-marks.
Knights of the Road, Knights of the Rail is a role-playing game set in the Great Depression. Players take on the characters of hoboes, those men and women of American folklore and myth, roaming the country in search of adventure. They travel across the United States and the mythical world of the Yonder, facing down railroad bulls, yeggs and mythical creatures. A different setting and a different kind of role-playing game.
(Thanks, Justin!)