Home › Words › T › trailhandtrailhandtrailhand means A cowboy or skilled horseman who routinely rides through the rural countryside.EtymologyFrom trail + hand.nounA cowboy or skilled horseman who routinely rides through the rural countryside.e.g.“I've gone horseback riding many times since I was a little girl, and my 9-year-old daughter Emily considered herself an old trailhand.” — 2003 July 6, Sara Campbell, “When a horseback ride turns into horror on the hoof”, in The Dallas Morning News:In the Old West, a mounted worker employed on a cattle drive.Definitions & examples from Wiktionary (CC BY-SA 3.0).