Green’s Dictionary of Slang

1. (also hit it, hit the breeze, hit the hike, hit the trail) to leave, to set out on a journey; thus imper. hit the road/hit the road, Jack, get out, go away.

1895		J. London ‘’Frisco Kid’s Story’ in High School Aegis X 15 Feb. 2–3: I found dat de kid’d run away from home an’ jest hit de road.
1904		Number 1500 Life In Sing Sing 256: Hitting the Road. Traveling.
1915		M.G. Hayden ‘Word List From Montana’ in DN IV:iii 244: hit the breeze, hike, trai., v. phr. = hit the road, to set off on the road, usually walking. ‘About ten I hit the hike’.
1919		‘Hit the Road’ in J.J. Niles Singing Soldiers (1927) 128: Oh, it’s hit the road, you lousy bums, / You stiffs and weary Willies.
1925		Dos Passos Manhattan Transfer 121: Every spring I says to myself I’ll hit the road again [...] but I dont.
1933		J.T. Farrell ‘Wedding Bells Will Ring’ in Short Stories (1937) 203: I guess I’d better be hitting it.
1933		M. Marshall Tramp-Royal on the Toby 8: I lost no time in hitting the road.
1946		H.A. Smith Rhubarb 103: Hit the road, toad! [...] Get out of this house!
1953		Mad mag. Apr.–May 7: Amscray! Agitate the gravel! Hit the road! Strike the pavement!
1957		Kerouac On The Road (1972) 26: Their old men had given them leave to hit the road for a summer.
1966		H.S. Thompson Hell’s Angels (1967) 163: Fill up at a cut-rate gas station and hit the road, with a pint on the seat and Eddy Arnold on the radio.
1972		B. Rodgers Queens’ Vernacular 107: hit it [...] 2. to make tracks, run.
1979		E. Torres After Hours 48: We picked up our gear and hit the road.
1983		R. Price Breaks 256: Here he was telling me to hit the road at sixteen.
1993		Tarantino & Avery Pulp Fiction [film script] 110: Honey, we gotta hit the fuckin’ road!
2004		P. Howard PS, I Scored the Bridesmaids 146: I head into the bathroom and tell her I’m hitting the road.

2. to leave prison.

2000

Observer Rev. 13 Feb. 4: Muff’s doing a nine stretch. Aggravated burglary. If he’s lucky he’ll hit the road in 2006.

3. to take up a life of crime.

1900

Flynt & Walton Powers That Prey 198: I hate to see a kid who’s been brought up decent hit the road. With me ’t was different. Both my old folks was crooks.