A History of Highwaymen

By Tim Lambert

The idea of robbing people while they travel along roads is a very old one. In the Middle Ages, there were plenty of outlaws ready to rob travelers. However, the ‘golden age’ of highwaymen was the 17th century and 18th century. At that time trade and commerce were increasing and there were many well-to-do travelers.

However, Britain was still a pre-industrial country. The population was small and there were vast areas of forest and other countryside where highwaymen could lie in wait. The invention of the flintlock pistol early in the 17th century also made life easy for highwaymen. Furthermore, Britain did not have a professional police force, which made it harder to catch them. The most dangerous roads were those around London.

There is a popular image of the highwayman as a gentleman and surprisingly some highwaymen were from quite wealthy backgrounds. Perhaps it was an exciting way of life being a highwayman but it was usually a short one – most were caught and hanged before they were 35.

Sometimes the travelers fought back. Many stagecoaches carried armed guards and some passengers carried pistols. There were also large rewards for anyone who could capture a highwayman and bring him to justice. Most highwaymen were eventually caught and hanged. Afterward, their body was sometimes hanged on a frame called a gibbet as a warning to others. On 25 April 1792 highwayman Nicolas Jacques Pelletier became the first person in France to be guillotined.

However, from the end of the 18th century policing of the highways greatly improved, and by the 1830s the age of the highwayman was over.

Dick Turpin

The most infamous highwayman is Dick Turpin. Although he is sometimes depicted as a dashing figure Turpin was actually a callous thug. He was born in 1705 in Essex. Turpin served an apprenticeship as a butcher but he soon turned to crime. At first, Turpin tried smuggling and rustling livestock. Later Turpin joined a gang of robbers north of London. (They robbed people in their homes). Later he became a highwayman in the same area. Turpin eventually moved to York where he lived under the name John Palmer.

However, he was arrested in October 1738 after he shot a gamecock and the authorities soon realized who they were dealing with. Turpin was tried and then hanged in April 1739. Legally Turpin was hanged for horse stealing.


Not all highwaymen were men! There were also highway women. Among them was Joan Bracey, who was hanged in 1685. Other notorious highway women were Mary Frith, known as Moll Cutpurse, and Catherine Ferrers.