1782, "highway robber," probably from dialectal verb scamp "to roam" (1753, perhaps from 16c.), which is shortened from scamper. By 1808 in a general sense of "fugitive, vagabond, swindler, mean villain;" used in the affectionate sense of "rascal" since 1837.
1560s, "idle vagrant, sturdy beggar, one of the vagabond class," a word of shadowy origin, perhaps a shortened form of roger (with a hard -g-), thieves' slang for a begging vagabond who pretends to be a poor scholar from Oxford or Cambridge, which is perhaps an agent noun in English from Latin rogare "to ask." Another theory [Klein] traces it to Celtic (compare Breton rog "haughty"); OED says, "There is no evidence of connexion with F. rogue 'arrogant' " (the theory supported in Century Dictionary).
By 1570s, generally, as "dishonest, unprincipled person, rascal." In slight playful or affectionate use, "one who is mischievous," 1590s. Meaning "large wild beast living apart from the herd" is by 1859, originally of elephants. As an adjective, in reference to something uncontrolled, irresponsible, or undisciplined, by 1964. Also common in 17c. as a verb. Rogue's gallery "police collection of mug shots of notorious law-breakers" is attested from 1859.
1590s, enterloper, "unauthorized trader trespassing on privileges of chartered companies," probably a hybrid from inter- "between" + -loper (from landloper "vagabond, adventurer," also, according to Johnson, "a term of reproach used by seamen of those who pass their lives on shore"); perhaps from a dialectal form of leap, or from Middle Dutch loper "runner, rover," from lopen "to run," from Proto-Germanic *hlaupanan "to leap" (see leap (v.)).
OED says Dutch enterlooper "a coasting vessel; a smuggler" is later than the English word and said by Dutch sources to be from English. General sense of "self-interested intruder" is from 1630s.
"to convict quickly and perhaps unjustly," 1873, American English, from railroad (n.) as the then-fastest form of travel.
A person knowing more than might be desirable of the affairs, or perhaps the previous life of some powerful individual, high in authority, might some day ventilate his knowledge, possibly before a court of justice; but if his wisdom is railroaded to State's prison, his evidence becomes harmless. ["Wanderings of a Vagabond," New York, 1873]
Related: Railroaded; railroading. An earlier verb sense was "to have a mania for building railroads" (1847).
The Dutch word is said to be cognate with Old English lutian "lurk," and related to Old English loddere "beggar;" Old High German lotar "empty, vain," luzen "lurk;" German Lotterbube "vagabond, rascal," lauschen "eavesdrop;" Gothic luton "mislead;" Old English lyðre "base, bad, wicked." Related: Loitered; loitering.