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Answer:
HOBOES
Possible Questions:
Vagrants
Bums
Rail riders
Tramps
Drifters
Bindlestiffs
Bindle carriers
Roads scholars
Runagates
Landlopers
Boxcar hoppers
Nomads in a long John Hodgman list
Depression stereotypes
Cross-country trainers?
Beggars of a sort
"Kings of the Road"