Etymology
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Words related to trail

tract (n.1)
"area," mid-15c., "period or lapse of time," from Latin tractus "track, course, space, duration," lit, "a drawing out or pulling," from stem of trahere "to pull, draw," from PIE root *tragh- "to draw, drag, move" (source also of Slovenian trag "trace, track," Middle Irish tragud "ebb;" perhaps with a variant form *dhragh-; see drag (v.)). The meaning "stretch of land or water" is first recorded 1550s. Specific U.S. sense of "plot of land for development" is recorded from 1912; tract housing attested from 1953.
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trailblazer (n.)
by 1893, from trail (n.) + agent noun from blaze (v.3).
trailer (n.)
1580s, "hound or huntsman that follows a trail," agent noun from trail (v.). From 1610s as "Something that trails." From 1890 as "vehicle pulled by another;" originally a small carriage drawn along by a bicycle. Meaning "preview of a coming movie" first attested 1928. Trailer park "mobile home community" recorded by 1936. Trailer trash in use by 1986.
troll (v.)

late 14c., "to go about, stroll," later (early 15c.) "roll from side to side, trundle," probably from Old French troller, a hunting term, "wander, to go in quest of game without purpose" (Modern French trôler), from a Germanic source (compare Old High German trollen "to walk with short steps"), from Proto-Germanic *truzlanan.

Sense of "sing in a full, rolling voice" (first attested 1570s) and that of "fish with a moving line" (c. 1600) both are extended technical uses from the general sense of "roll, trundle," the former from "sing in the manner of a catch or round," the latter perhaps confused with trail or trawl. Figurative sense of "to lure on as with a moving bait, entice, allure" is from 1560s. Meaning "to cruise in search of sexual encounters" is recorded from 1967, originally in homosexual slang.

The internet sense (everyone seems to have his own definition of it) seems to date to the late 1980s or early 1990s and the Newsgroups era, and the verbal use is perhaps older than the noun. It seems to combine troll (v.) in the "fish with a moving line" sense (itself confused with trawl) and troll (n.1) "troublesome imp supposed to live underground."