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trail (v.)

c. 1300, "to hang down loosely and flow behind" (of a gown, sleeve, etc.), from Old French trailler "to tow; pick up the scent of a quarry," ultimately from Vulgar Latin *tragulare "to drag," from Latin tragula "dragnet, javelin thrown by a strap," probably related to trahere "to pull" (see tract (n.1)). Transitive sense of "to tow or pull along the ground" is from c. 1400. The meaning "follow the trail of" (an animal, etc.) is first recorded late 14c. Meaning "to lag behind" is from 1957. Related: Trailed; trailing.

trail (n.)

early 14c., "trailing part of a robe, gown, etc.," from trail (v.). The meaning "track or smell left by a person or animal" is also from 1580s. Meaning "path or track worn in wilderness" is attested from 1807. Trail of Tears in reference to the U.S. government's brutally incompetent Cherokee removal of 1838-9 is attested by 1908.

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Definitions of trail from WordNet
1
trail (v.)
to lag or linger behind;
Synonyms: drag / get behind / hang back / drop behind / drop back
trail (v.)
go after with the intent to catch;
Synonyms: chase / chase after / tail / tag / give chase / dog / go after / track
trail (v.)
move, proceed, or walk draggingly or slowly;
The Mercedes trailed behind the horse cart
John trailed behind his class mates
Synonyms: shack
trail (v.)
hang down so as to drag along the ground;
The bride's veiled trailed along the ground
trail (v.)
drag loosely along a surface; allow to sweep the ground;
The toddler was trailing his pants
Synonyms: train
2
trail (n.)
a track or mark left by something that has passed;
there as a trail of blood
a tear left its trail on her cheek
trail (n.)
a path or track roughly blazed through wild or hilly country;
trail (n.)
evidence pointing to a possible solution;
the trail led straight to the perpetrator
Synonyms: lead / track
From wordnet.princeton.edu