A highwayman was a robber who stole from travellers. This type of thief usually travelled and robbed by horse, as compared to a footpad who travelled and robbed on foot; mounted highwaymen were widely considered to be socially superior to footpads. Such robbers operated in Great Britain from the Elizabethan era until the early 19th century. In many other countries, they persisted for a few decades longer, until the mid or late 19th century.
The word highwayman is first known to have been used in the year 1617; other euphemisms included "knights of the road" and "gentlemen of the road". In the 19th-century American West, highwaymen were known as road agents. In Australia they were known as bushrangers.
The great age of highwaymen was the period from the Restoration in 1660 to the death of Queen Anne in 1714. Some of them are known to have been disbanded soldiers and even officers of the English Civil War and French wars; no doubt the warlike character of the age multiplied crimes of violence. What favoured them most was the lack of governance and absence of a police force: parish constables were almost wholly ineffective and commonplace detection and arrest were very difficult. Most of the highwaymen held up travellers and took their money. Some had channels by which they could dispose of bills of exchange. Others had a 'racket' on the road transport of an extensive district; carriers regularly paid them a ransom to go unmolested. Highwaymen, along with rioters and smugglers, defied the corrupt government of the time.
They often attacked coaches for their lack of protection, including public stagecoaches; the postboys who carried the mail were also frequently held up. The famous demand to "!" (sometimes in forms such as "Stand and deliver your purse!" "Stand and deliver your money!") was in use from the 17th century.
A fellow of a good Name, but poor Condition, and worse Quality, was Convicted for laying an Embargo on a man whom he met on the Road, by bidding him Stand and Deliver, but to little purpose; for the Traveller had no more Money than a Capuchin, but told him, all the treasure he had was a pound of Tobacco, which he civilly surrendered.