17th century phenomenon. Armed robbers would hold up coaches carrying rich passengers and shout, according to legend: "Stand and deliver! Your money or your life!" and force them to hand over jewellery and money.

Also, as of the early twentieth century it also refered to prison inmates who were assigned to build highways.

High"way`man (?), n.; pl. Highwaymen ().

One who robs on the public road; a highway robber.

© Webster 1913.