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 criminals operated until the mid- or late 19th century. Highwaywomen, such as Katherine Ferrers, were said to also exist, often dressing as men, especially in fiction.
The first attestation of the word highwayman is from 1617. In the 19th-century American West, highwaymen were sometimes known as road agents. In Australia, they were known as bushrangers, in India as Thugs.
Highwaymen were most prevalent in England from the Restoration in 1660 to the death of Queen Anne in 1714. Some are known to have been disbanded soldiers, and even officers, of the English Civil War and French wars. What favoured them most was the lack of governance and absence of a police force: parish constables were almost entirely ineffective, while 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.
They often attacked coaches for their lack of protection, including public stagecoaches; the postboys who carried the mail were also frequently held up. The demand to "Stand and deliver!" (sometimes in forms such as "Stand and deliver your purse!" "Stand and deliver your money!") was in use from the 17th century to the 19th 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.
The phrase "Your money or your life!" is mentioned in trial reports from the mid-18th century:
Evidence of John Mawson: "As I was coming home, in company with Mr. Andrews, within two fields of the new road that is by the gate-house of Lord Baltimore, we were met by two men; they attacked us both: the man who attacked me I have never seen since. He clapped a bayonet to my breast, and said, with an oath, Your money, or your life! He had on a soldier's waistcoat and breeches. I put the bayonet aside, and gave him my silver, about three or four shillings."
Victims of highwaymen included the Prime Minister Lord North, who wrote in 1774: "I was robbed last night as I expected, our loss was not great, but as the postilion did not stop immediately one of the two highwaymen fired at him (They had guns at the time) – It was at the end of Gunnersbury Lane." Horace Walpole, who was shot at in Hyde Park, wrote that "One is forced to travel, even at noon, as if one was going to battle." During this period, crime was rife and encounters with highwaymen could be bloody if the victim attempted to resist. The historian Roy Porter described the use of direct, physical action as a hallmark of public and political life: "From the rough-house of the crowd to the dragoons' musket volley, violence was as English as plum pudding. Force was used not just criminally, but as a matter of routine to achieve social and political goals, smudging hard-and-fast distinctions between the worlds of criminality and politics... Highwaymen were romanticized, with a hidden irony, as 'gentlemen of the road.'"
There is a long history of treating highway robbers as heroes. They were admired by many as bold men who confronted their victims face to face and were ready to fight for what they wanted. Medieval outlaw Robin Hood is regarded as an English folk hero. Later robber heroes included the Cavalier highwayman James Hind; the French-born gentleman highwayman Claude Du Vall; John Nevison; Dick Turpin; Sixteen String Jack; William Plunkett and his partner, the "Gentleman Highwayman" James MacLaine; the Slovak Juraj Jánošík; the Ukrainian Oleksa Dovbush; and Indians including Kayamkulam Kochunni, Veerappan, and Phoolan Devi. In the same way, the Mexican bandit Joaquin Murrieta during the California Gold Rush and the Puerto Rican pirate Roberto Cofresí also came to be venerated as heroes.
In early modern Ireland, acts of robbery were often part of a tradition of Irish Catholic resistance to the Dublin Castle administration and Protestant Ascendancy. From the mid-17th century onwards, Catholic highwaymen who harassed the Crown and their supporters were known as 'tories' (from Irish tóraidhe, raider; tóraí in modern spelling). By the end of the century, they were also known as rapparees. Notable Irish highwaymen of the period included James Freney, Redmond O'Hanlon, Willy Brennan and Jeremiah Grant.
English highwaymen often laid in wait on the main roads radiating from London. They usually chose lonely areas of heathland or woodland. Hounslow Heath was a favourite haunt: it was crossed by the roads to Bath and Exeter. Bagshot Heath in Surrey was another dangerous place on the road to Exeter. One of the most notorious places in England was Shooter's Hill on the Great Dover Road. Finchley Common, on the Great North Road, was nearly as bad.
To the south of London, highwaymen sought to attack wealthy travellers on the roads leading to and from the Channel ports and aristocratic arenas like Epsom, which became a fashionable spa town in 1620, and Banstead Downs where horse races and sporting events became popular with the elite from 1625. Later in the 18th century, the road from London to Reigate and Brighton through Sutton attracted highwaymen. Commons and heaths considered to be dangerous included Blackheath, Putney Heath, Streatham Common, Mitcham Common, Thornton Heath – also the site of a gallows known as "Hangman's Acre" or "Gallows Green" – Sutton Common, Banstead Downs and Reigate Heath.
During the late 17th and early 18th centuries, highwaymen in Hyde Park were sufficiently common for King William III to have the route between St James's Palace and Kensington Palace (Rotten Row) lit at night with oil lamps as a precaution against them. This made it the first artificially lit highway in Britain.
The penalty for robbery with violence was hanging, and most notorious English highwaymen ended on the gallows. The chief place of execution for London and Middlesex was Tyburn Tree. Highwaymen whose lives ended there include Claude Du Vall, James MacLaine, and Sixteen-string Jack. Highwaymen who went to the gallows laughing and joking, or at least showing no fear, are said to have been admired by many of the people who came to watch.
During the 18th century, French rural roads were generally safer from highwaymen than those of England, an advantage credited by the historian Alexis de Tocqueville to the existence of a uniformed and disciplined mounted constabulary known as the Maréchaussée. In England this force was often confused with the regular army and as such cited as an instrument of royal tyranny not to be imitated.
In England, the causes of the decline are more controversial. After about 1815, mounted robbers are recorded only rarely, the last recorded robbery by a mounted highwayman having occurred in 1831. The decline in highwayman activity also occurred during the period in which repeating handguns, notably the pepper-box and the percussion revolver, became increasingly available and affordable to the average citizen. The development of the railways is sometimes cited as a factor, but highwaymen were already obsolete before the railway network was built. The expansion of the system of turnpikes, manned and gated toll-roads, made it all but impossible for a highwayman to escape notice while making his getaway, but he could easily avoid such systems and use other roads, almost all of which outside the cities were flanked by open country.
Cities such as London were becoming much better policed: in 1805 a body of mounted police began to patrol the districts around the city at night. London was growing rapidly, and some of the most dangerous open spaces near the city, such as Finchley Common, were being covered with buildings. However, this only moved the robbers' operating area further out, to the new exterior of an expanded city, and does not therefore explain decline. A greater use of banknotes, more traceable than gold coins, also made life more difficult for robbers, but the Inclosure Act 1773 was followed by a sharp decline in highway robberies; stone walls falling over the open range like a net, confined the escaping highwaymen to the roads themselves, which now had walls on both sides and were better patrolled.