Green’s Dictionary of Slang

1. a person who goes out looking for sex.

1621		R. Burton Anatomy of Melancholy (1850) 558: I could not abide marriage, but as a rambler [...] I took a snatch where I could get it; nay more, I railed at marriage downright.
1672		Wycherley Gentleman Dancing-Master I ii: We are not so much afraid to be taken up by the Watch, as by the taring midnight Ramblers or Houza-Women.
c.1689		ballad title in Pepys Ballads (1987) III 294: The Female Ramblers.
1772		G. Stevens ‘Mutual Love’ in Songs Comic and Satyrical 110: She languishing lay in Love’s tenderest scene, / And question’d the Rambler where ’twas he had been?
1823		Account of Mary M’Kinnon 49: Now all you Ramblers, in mourning go, / For the Queen of Ramblers must lye low.
1825		C.M. Westmacott Eng. Spy I 204: His deaf-lugg’d daddy a known blade / In Pandemonium’s fruitful trade, / ’Mong Paphians a rambler.
c.1880		broadside ballad title Rambling Boys of Pleasure.
1928		L. Johnson ‘Crowing Rooster Blues’ 🎵 What makes a rooster crow every morning ‘fore day? / To let the pimps and ramblers know that the working man is on his way.
1964		R.D. Abrahams Deep Down in the Jungle 192: ‘Now all you no-good, you midnight ramblers, alcoholics, late players, out-stayers, wife-beaters, children deserters, get over on the other side of the room’.

2. (US tramp, also rambler wolf) a tramp who travels on passenger trains.

1916		‘A-No. 1’ Snare of the Road 31: in accordance with the method of travel they prefer when hoboing over the country, tramps are classed in three grand divisions: ‘Pikers’ they are called who walk; ‘Rattlers,’ who ride freight cars, and ‘Ramblers,’ who hobo passenger trains.
1927		‘Jargon of the Und.’ in DN V 460: Rambler, A high class tramp who rides only passenger trains. There are two classes of ramblers, the foxes who ride inside by stealing hat checks, clambering into women’s toilets, etc., and the wolves who ride by brute force.
1931		Irwin Amer. Tramp and Und. Sl. 154: Rambler.–A high-class tramp or hobo, one who rides only fast passenger trains, and usually for long distances.
1949		Monteleone Criminal Sl. (rev. edn) 189: rambler wolf A tramp who rides passenger trains.
1965		B. Jackson Get Your Ass in the Water (1974) 73: Now I’m a number one rambler of request, / I’m known in every burg around Chicago, / from Paris to Key West.