Green’s Dictionary of Slang

1. to live or travel as a tramp.

1893		Sun (NY) 21 May 28/1: ‘Dis is de last time dat I’m goin’ to get on de hog [...] Dis is de fourt’ winter dat I’ve had to “hobo” it and I’m tired’.
1906		U.B. Sinclair Jungle xxv 298: Then he explained how he had spent the last summer, ‘hoboing it,’ as the phrase was.
1914		Day Book (Chicago) 17 Aug. 19/1: It’s one hundred and fifty miles to your home, say say. You might hobo it, there’s no freighter out of this town.
1917		‘A-No. 1’ From Coast to Coast with Jack London 42: Our determination to hobo his train in spite of his orders to the contrary.
1924		‘Digit’ Confessions of a Twentieth Century Hobo 31: Let’s hobo south down Florida way.
1937		‘Boxcar Bertha’ Sister of the Road (1975) 33: I had thought of my trip in terms of hoboing and hobo I would.
1941		A. Lomax Mister Jelly Roll (1952) 134: Jack the Bear proposed that we hobo.
1955		B. Appel Tough Guy [ebook] ‘Joey, les hobo a while. I always wanted to see the country’.
1960		T. Draper Amer. Communism and Soviet Russia (2003) 62: He hoboed his way up and down and across the country.
1973		H. Armstrong in Heller In This Corner (1974) 201: It was in the early thirties, there was a lot of hoboing going on.
1976		in E. Wigginton ‘I Wish I Could Give My Son a Wild Raccoon’ 41: He just hoboed all over the country. He never had no stopping place.
1996		C. Abrams Silents 3: [...] the days when he hoboed through America in search of adventure.
2000		B.K. Garman A Race of Singers 146: Dylan reinvented himself as a weary traveler who had hoboed around the country for most of his young life.

2. in fig. use, i.e. to travel or catch a free train ride.

1979

‘Iceberg Slim’ Airtight Willie and Me 75: I hoboed heroin’s express train to you know where.