A highwayman was a robber who stole from travelers. 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 "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.
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 Proceedings of the Old Bailey, 25 April 1677, 
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."— The Proceedings of the Old Bailey, 12 September 1781, 
There were many famous victims of highwaymen. The Prime Minister Lord North wrote in 1774: "I was robbed last night as I expected, our loss was not great, but as the postillion did not stop immediately one of the two highwaymen fired at him - It was at the end of Gunnersbury Lane." Horace Walpole, shot at in Hyde Park, wryly observed, "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'."
Robbers as heroes
There is a long history of treating highway robbers as heroes. Originally they were admired by many as bold men who confronted their victims face-to-face and were ready to fight for what they wanted. The most famous English robber hero is the legendary medieval outlaw Robin Hood. 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, and Indians including Kayamkulam Kochunni, Veerappan and Phoolan Devi.
In 17th- through early-19th-century Ireland, acts of robbery were often part of a tradition of popular resistance to British colonial rule and settlement and Protestant domination. From the mid-17th century, bandits who harassed the British were known as tories (from Irish tórai, raider). Later in the century, they became known as rapparee. Famous highwaymen included James Freney, Count Redmond O'Hanlon, Willy Brennan, and Jeremiah Grant.
Highwaymen often lay 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, England. 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 (Great Britain), was very 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. Famous 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 occurred during the period in which repeating handguns, notably the pepperbox 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 Enclosure Act  of 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. The dramatic population increase which began with the Industrial Revolution also meant, quite simply, that there were more eyes around, and the concept of the remote place, in England became a thing of the past.
Outside Anglophone countries
The Holy Land
Tradition identifies Saint Dismas, or the Penitent Thief, as a highwayman. Crucified with Jesus Christ, he repented of his sins and was told by Jesus, "This day you shall be with Me, together in paradise."
The bandits in Greece under Ottoman rule were the Klephts (κλέφτες), Greeks who had taken refuge in the inaccessible mountains. The klephts, who acted as a guerilla force, were instrumental in the Greek War of Independence.
Hungary and Slovakia
The highwaymen of 18th- and 19th-century Kingdom of Hungary were the betyárs. Until the 1830s they were mainly simply regarded as criminals but an increasing public appetite for betyar songs, ballads and stories gradually gave a romantic image to these armed and usually mounted robbers. Several of the betyárs have become legendary figures who in the public mind fought for social justice. The most famous Hungarian betyárs were Sándor Rózsa (Slovak: Šaňo Róža), Jóska Sobri, Márton Vidróczki, Jóska Savanyú. Slovakia's Juraj Jánošík (Hungarian: György Jánosik) is still regarded as the Slovakian Robin Hood.
The Indian Subcontinent has had a long and colorful history of organised robbery for millennia. Most famous of these were the Thuggees, a quasi-religious group that robbed travellers on Indian roads until the cult was systematically eradicated in the mid-1800s by British colonial administrators. Thugees would befriend large road caravans, gain their confidence, strangle them to death at the right moment, and then rob them of their valuables. According to some estimates the Thuggees murdered 1 million people between 1740 and 1840. More generally, armed bands known colloquially as "dacoits" have long wreaked havoc on many parts of the country. In recent times this has often served as a way to fund various regional and political insurgencies that includes the Maoist Naxalite movement.
Serbia, Bosnia and Croatia
The bandits in Serbia, Bosnia and Croatia under Ottoman rule were the Hajduks (Hajduci, Хајдуци), rebels who opposed Ottoman rule and acted as a guerilla force, also instrumental in the many wars against the Ottomans and especially the Serbian revolution. Serbian and Croatian refugees in Austro-Hungarian (and Habsburg) lands were also part of the Uskoci. Notable freedom fighters include Starina Novak, a notable outlaw was Jovo Stanisavljević Čaruga.
- List of highwaymen
- Road agent
- Mail robbery
- Social bandits
- Rid, Samuel. "Martin Markall, Beadle of Bridewell," in The Elizabethan Underworld, A. V. Judges, ed. pp. 415–416. George Routledge, 1930. Online quotation. See also Spraggs, Gillian: Outlaws and Highwaymen: the Cult of the Robber in England from the Middle Ages to the Nineteenth Century, pp. 107, 169, 190–191. Pimlico, 2001.
- Fennor, William. "The Counter’s Commonwealth," in The Elizabethan Underworld, p. 446.
- Brewer, E. Cobham. Dictionary of Phrase and Fable, 1898, defines road-agent as "A highwayman in the mountain districts of North America," citing the generation earlier, W. Hepworth Dixon, New America, p. 14: "Road-agent is the name applied in the mountains to a ruffian who has given up honest work in the store, in the mine, in the ranch, for the perils and profits of the highway."
- Clark, Sir George (1956). The Later Stuarts, 1660-1714. Oxford History of England: Oxford University Press. p. 259. ISBN 0-19-821702-1.
- Beattie, J. M.: Crime and the Courts in England, 1660–1800, pp. 149–158. Clarendon Press, 1986; Extracts from Wilson, Ralph: A Full and Impartial Account of all the Robberies Committed by John Hawkins, George Sympson (lately Executed for Robbing the Bristol Mails) and their Companions. 3rd edition, J. Peele, 1722.
- The Proceedings of the Old Bailey: fellow, theft with violence : highway robbery, 25th April, 1677.
- The Proceedings of the Old Bailey born in 1706: JOHN BUCKLEY, THOMAS SHENTON, theft with violence : highway robbery, 12th September, 1782.
- Porter, Roy (1982). English Society In The Eighteenth Century. Pelican Social History of Britain: Pelican Books. p. 31, 114-115. ISBN 0-14-022099-2.
- Spraggs, Gillian: Outlaws and Highwaymen: the Cult of the Robber in England from the Middle Ages to the Nineteenth Century, pp. 2–3, 7–8, 255. Pimlico, 2001.
- Dunford, Stephen. The Irish Highwaymen. Merlin Publishing, 2000
- Seal, Graham. The Outlaw Legend: a cultural tradition in Britain, America and Australia, pp. 69–78. Cambridge University Press, 1996.
- Maxwell, Gordon S. : Highwayman's Heath: Story in Fact and Fiction of Hounslow Heath in Middlesex . Heritage Publications, Hounslow Leisure Services, 1994.
- Beattie, J. M.: Crime and the Courts in England, 1660–1800, pp. 155–156. Clarendon Press, 1986; Spraggs, Gillian: Outlaws and Highwaymen: the Cult of the Robber in England from the Middle Ages to the Nineteenth Century, p. 93. Pimlico, 2001. Harper, Charles George: Half-hours with the Highwaymen: picturesque biographies and traditions of the "knights of the road", pp. 245–255. Chapman & Hall, 1908; Online edition of Half-hours with the Highwaymen. via Internet Archive.
- Walford, Leslie (7 March 2011). "Stand and Deliver!". Time & Leisure. Retrieved 27 December 2016.
- Hibbert, Cristopher; Weinreb, Ben; Keay, John; Keay, Julia (2011). The London Encyclopaedia. Pan Macmillan. p. 424. ISBN 0230738788.
- Spraggs, Gillian: Outlaws and Highwaymen: the Cult of the Robber in England from the Middle Ages to the Nineteenth Century, pp. 212–233. Pimlico, 2001
- Alexis de Tocqueville L'Ancien Régime et la Révolution
- McLynn, Frank: Crime and punishment in eighteenth-century England, p. 81. Routledge, 1989.
- Spraggs, Gillian: Outlaws and Highwaymen: the Cult of the Robber in England from the Middle Ages to the Nineteenth Century, p. 234. Pimlico, 2001.
- 'The Enclosure Acts and the Industrial Revolution', Wendy McElroy, 2012
- SHP History B-- Crime and Punishment 1750 - 1900, 3.3 Highwaymen. https://www.pearsonschoolsandfecolleges.co.uk/FEAndVocational/Humanities/History/EdexcelGCSESHPHistory2013/Samples/Crime(1B)andProtest(3B)/HistoryB1BHighwaymenpreview.pdf
- 'The Ecological Impact of the Industrial Revolution', Eric McLamb, 2011 http://www.ecology.com/2011/09/18/ecological-impact-industrial-revolution/
- Rubinstein, W. D. (2004). Genocide: a history. Pearson Education. pp. 82–83. ISBN 0-582-50601-8.
- Ash, Russell (1970). Highwaymen, Shire Publications, ISBN 978-0-85263-101-0; revised edition (1994) ISBN 978-0-7478-0260-0
- Billett, Michael (1997). Highwaymen and Outlaws, Weidenfeld Military, ISBN 978-1-85409-318-9
- Brandon, David (2004). Stand and Deliver! A History of Highway Robbery, Sutton Publishing, ISBN 978-0-7509-3528-9
- Dunford, Stephen (2000). The Irish Highwaymen, Merlin Publishing, ISBN 1-903582-02-4
- Evans, Hilary & Mary (1997). Hero on a Stolen Horse: Highwayman and His Brothers-in-arms – The Bandit and the Bushranger, Muller, ISBN 978-0-584-10340-3
- Haining, Peter (1991). The English Highwayman: A Legend Unmasked, Robert Hale, ISBN 978-0-7090-4426-0
- Harper, Charles George (1908). Half-hours with the Highwaymen: picturesque biographies and traditions of the "knights of the road", Chapman & Hall. Online edition, via Internet Archive.
- Hobsbawm, Eric (1969). Bandits, Delacorte Press; Revised edition (2000). ISBN 978-1-56584-619-7
- Koliopoulos, John S (1987). Brigands with a Cause, Brigandage and Irredentism in Modern Greece 1821–1912. Clarendon Press. ISBN 978-0-19-822863-9
- Maxwell, Gordon S (1994). Highwayman's Heath: Story in Fact and Fiction of Hounslow Heath in Middlesex , Heritage Publications, Hounslow Leisure Services, ISBN 978-1-899144-00-6
- Newark, Peter (1988). Crimson Book of Highwaymen, Olympic Marketing Corp, ISBN 9789997354792
- Pringle, Patrick (1951). Stand and Deliver: The Story of the Highwaymen, Museum Press, ASIN B0000CHVTK
- Seal, Graham (1996). The Outlaw Legend: a cultural tradition in Britain, America and Australia, Cambridge University Press, ISBN 0-521-55317-2 (hbk), ISBN 0-521-55740-2 (pbk)
- Sharpe, James (2005). Dick Turpin: The Myth of the English Highwayman, Profile Books, ISBN 978-1-86197-418-1
- Spraggs, Gillian (2001). Outlaws and Highwaymen: The Cult of the Robber in England from the Middle Ages to the Nineteenth Century, Pimlico, ISBN 978-0-7126-6479-0
- Sugden, John and Philip (2015). The Thief of Hearts: Claude Duval and the Gentleman Highwayman in Fact and Fiction, Forty Steps, ISBN 978-0-9934183-0-3
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