highwayman

Highwayman refers to a robber who targeted travelers on roads, usually while mounted on horseback. The term is most closely associated with early modern Britain, particularly along coaching routes in the 17th and 18th centuries, though similar figures operated elsewhere. Highwaymen typically stopped riders or coaches, demanded valuables, and fled on horseback. The practice contributed to the development of policing and travel security, and it entered popular folklore and ballads as a symbol of daring outlawry.

Historical highway robbery flourished on major routes during the reigns of the Stuarts and early Georgian era, when long-distance travel with coaches and carts was common. Offenders used masks, pistols or sabers, and often worked in small gangs or waited at isolated inns. Victims ranged from aristocrats to merchants; some coaches were attacked with staves or tricks to force passengers to surrender. Legal response included local magistrates, colonial and urban constabularies, and, later, organized patrols such as the Bow Street Runners; punishments included hanging or transportation.

Notable highwaymen include several celebrated figures in British folklore and literature, whose stories emphasize audacity and style. The image of the highwayman has been cultivated in ballads, stage plays, dime novels, and films, contributing to a romanticized stereotype of the outlaw of the road. In modern usage, "highway robbery" survives as a general term for armed robbery on roads or gross overcharging, though it is now a legal and economic phrase in various jurisdictions.