hobby hobo
n. A part-time hobo; a person who engages in hobo-like behaviour — such as hopping freight trains — while on vacation from their full-time job.
Mr. Kazda has been a freight-hopper for 10 years. His girlfriend, Nina Bains, has been doing it for three.
When he decides to hit the rails in search of an authentic American experience, National Book Award-winning author and novelist William T. Vollmann (Europe Central; Rising Up and Rising Down) is indulging a romantic fantasy that runs through the literature of the United States like the tracks once laid from New York to San Francisco….

An internationally applauded author, journalist and chronicler of the human dark side, Vollmann becomes a hobby hobo when his pique at 21st century America…drives him in the only direction any self-respecting, U.S.A.-made, ruggedly individualistic iconoclast can be driven, and that's toward the (ahem) frontier.
—Geoff Pevere, “Lighting out for the territories,” The Toronto Star, March 02, 2008
1998 (earliest)
'They really live lives that are creative, imaginative and free,' Minneapolis Skinny said. 'And it's disappearing.' Skinny is one of those hobby hobos whose lives are 99 per cent straight.
—“Real travel, real people,” Vagabond Monthly, July 01, 1998
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