Stand and Deliver: Who Were Britain’s Highwaymen?

Legends of highwaymen and roadside robbers have sparked fear and awe in people across Britain for generations.

Active all the way up until the mid to late 1800s, these storied criminals inspired songs and legends and became a prominent part of British folk history. Usually travelling by horse, highwaymen and highwaywomen were criminals who stopped and robbed travellers on the road. They were active throughout Britain and operated across other countries as well.

Despite their criminal, and at times violent, activities, highwaymen gained social prominence and were romanticised as charming and popular figures of society. While the life of a highwayman was fraught with risk, people from across the economic and social spectrum participated in this shady business.

Accounts of rebel heiresses and well-dressed thieves were carried across the English countryside as bold roadside robbers targeted everyone from civilian travellers to the President of the High Court of Justice on Britain’s lonely laneways.

Dick Turpin
Most highwaymen were really no more than thugs

To this day, highwaymen hold a unique place in hearts and minds. Their legacy as charming and adventurous roadside thieves has endured. These prominent members of British folklore have inspired arts and culture, and captured imaginations since they roamed the roads of Britain.


Highwaymen posed a significant risk for those travelling the British countryside prior to the mid to late 1800s. Poorly guarded coaches, which often transported valuable goods and wealthy citizens, were particularly alluring targets for these criminals.

Highwaymen were noted to work as both bands of criminals and as lone thieves. While many simply stopped travellers and robbed them on the road, some also developed rackets over districts where transport organisations and individual travellers paid highwaymen to travel through the district undisturbed.

Highwaymen in a woodland
Highwaymen would often wait for their victims in woodlands where they could simply just melt away after the robbery.

Travel at Your Own Risk

Roadside thievery from highwaymen and other criminals was noted to be a particular issue from the mid-1600s to 1714. A lack of effective governance or an efficient police force during this period lent itself to a significant rise in criminal activities.

The mid-1600s also marked the immediate aftermath of the English Civil War, already trained for combat and disbanded from the army, many soldiers turned against king and country to enter into a life of crime as a means of sustaining themselves.

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Neither the rich nor the poor were safe when travelling Britain’s historic roadways with accounts that even Lord North, then Prime Minister of Great Britain, was robbed on the road in 1774.

There were areas and roadways that were known as places where highwaymen were exceedingly active. These areas often were surrounded by woodlands or heaths where travellers were isolated and far from help.

royal mail coach
A coach in 1838 was only comfortable for the four people inside the coach. You can see the guard at the back who was to protect from the highwaymen

Highway From Hell

Both Hounslow Heath and the road between Epsom and Channel were areas where highwaymen were reputed to be feared. Highwaymen posed such a threat that King William III is said to have had the road between Kensington Palace and St. James Palace lit with oil lamps after dark to deter attacks from thieves.

One road and route that was feared by passengers and travellers was the main Portsmouth to London Road. The number of wealthy travellers was too much for the highwaymen who operated in that part of Hampshire.

Being used extensively by rich naval officers and sailors on leave. As the port grew so did London bound stage coaches, it is thought that by 1820 up to one hundred coaches travelled the road every week and took nine hours to complete the seventy one mile journey.

An isolated section of the route just south of Petersfield became a ‘highway from hell’.

In 1895, author Charles Harper, wrote about the Portsmouth Rd “… our forebears who prayerfully entrusted their bodies to the dangers of the roads and resigned their souls to Providence, were hurried along this route at the breakneck speed of something under eight miles an hour, with their hearts in their mouths and their money in their boots for fear of the highwaymen who infested the roads…”  

the ROCKET stage coach poster
Advert for the new ROCKET coach on the London – Portsmouth route which took nine hours door to door.

The outriders would carry weapons, mainly cutlasses and flintlock blunderbusses to defend the passengers, and themselves against the highwaymen. Murder became so common place along this section that it earned the infamous name of the Road of Assassination.

Romance and the Gallows

Despite the violent activities of highwaymen, they gained a somewhat romanticised reputation that has endured into modern times. Many were viewed as ‘gentlemen of the road’ and were respected for their bold and upfront approach.

However, this romanticised reputation didn’t save them from the wrath of the law. The Act of Parliament for the Apprehending of Highwaymen came into effect in 1692. This act gave monetary rewards for the capture of highwaymen and incentivised those that had turned to a life of crime to turn on each other by offering immunity to those that gave up their accomplices.

Living the life of a highwayman was a dangerous existence. Many suffered injury or met their deaths while engaging in their illegal activities and for those that were captured, the fate waiting for them was the gallows or transportation.

A number of highwaymen met their end at Tyburn Tree in Middlesex, and in 1776, James Snook, also known as The Robber Snook and Robert Snooks, became the last person to be executed on the charge of highway robbery in England.

While the activities of mounted roadside thieves became less prominent towards the end if the eighteenth century, the death of James Snook did not mark the end of the wrath of highwaymen in England.

Old Mobb highwayman
Highwayman Old Mobb from Romsey became a legend in Hampshire’s history. He was eventually caught in London. One account said: of Old Mobb “He rarely murdered his victims, never tortured them, frequently blew them kisses, and was even willing to accept cheques.’’ Some historians said Old Mobb never married and when he met his end at the end of a hangman’s noose he was still dressed as a woman.

Gentlemen Thieves and Rebel Heiresses

While many people engaged in highway robbery, there were some who gained an especially prominent status. From gentlemen thieves to formidable women, these individuals on the wrong side of the law became the stuff of legends.

One highwayman Old Mobb, a highwayman from Romsey, Hampshire would blow a kiss to those he had just robbed. It didn’t really work because on May 30, 1690 he was executed. 

Katherine Ferrers

Gaining the moniker, The Wicked Lady, Lady Katherine Ferrers rose to prominence as a highwaywoman in the mid-1600s. Born to a wealthy family in Hertfordshire, Katherine was the sole heir to her family’s extensive estate.

Despite her privileged position early in life, Katherine is said to have turned to highway robbery after her husband died, much of her estate was sold and her fortunes began to fall into ruin.

Legend has it that Katherine, dressed in men’s clothes, robbed travellers throughout Hertfordshire. Katherine died at just twenty-six, supposedly on the steps of her family’s estate, meeting her end as the result of a gunshot wound obtained in a robbery.

While there is speculation around the accuracy of the tales of Katherine’s life of crime, she is remembered as a striking figure of Britain’s social history.

James Hind

Cited as a potential inspiration for the legend of Robin Hood, James Hind was a seventeenth century highwayman that robbed wealthy Commonwealth forces and gave money to poor Royalists.

Fighting for the Royalist side during the English Civil War, James is said to have even played a part in assisting King Charles II escape after his defeat at the Battle of Worcester.

Disillusioned with the English Commonwealth, after the defeat of Royalists in the war, James turned to a life as a highwayman. James gained a reputation as a gentleman thief, noted for his polite and charming demeanour, even when stealing from his victims.

Hind gained notoriety across England for his life as a highwayman and is said to have even robbed the President of the High Court of Justice, and to have unsuccessfully attempted to rob Oliver Cromwell.

James was eventually captured and was charged with the severe crime of treason due to his Royalist sympathies. He met a grisly end, being hung, drawn and quartered in 1652.

John Rann

Known as ‘Sixteen String Jack’, John Rann was an eighteenth-century highwayman from Somerset. Known for donning eccentric and expensive clothing, it is said that his unusual nickname was on account of the sixteen coloured silk strings on the knees of his breeches.

Having gained a taste of the high life while working in London, he was noted for often living beyond his means and funding an extravagant lifestyle may well have been what drove him to a life of crime to begin with.

Rann was arrested on several occasions but due to lack of evidence and witnesses he was released. As well as his recognisable dress style, he was known for his wit and charming personality.

At the age of just twenty-four he was again arrested and sentenced to death, it is said that the night before his execution he entertained guests at Newgate Gaol and joked with the hangman at his execution.

Claude Duval

While highwaymen were often romanticised as a charming group, none quite gained the same reputation for charm as Claude Duval. Born to a family of ruined French nobility, Claude is thought to have come to England during the English Restoration.

Working as a highwayman, he robbed travellers on their way to London. Legend has it that he was exceptionally charming and courteous, particularly with women, and adopted a nonviolent approach when robbing his victims.

In 1670, Duval was captured and hung on six accounts of robbery. The church in which he is supposedly buried has a memorial to Duval including the phrase, If male thou art,

Look to thy purse; if female, to thy heart.

The Decline of Roadside Robbery

By the 1830s, highwaymen had become an infrequent risk of British travel. The last robbery by a mounted assailant was in 1831. The decline of highwaymen is believed to be the result of several contributing factors.

Better policing and the expansion of manned and gated toll roads made it more difficult for highwaymen to engage in their illegal activities and make a quick and undetected escape.

Around the same time as the decline of highwaymen, small guns and pistols were becoming more available for regular citizens to obtain and banknotes and gold coins were becoming more traceable, making it increasingly hard for highway thieves.

The declining frequency of highwaymen may also have been in part since the population of Britain was rapidly expanding. This growing population led to expanding towns and cities, meaning there were simply fewer isolated places for highwaymen to ambush travellers and escape to afterwards.

The Legacy of the Highwaymen

Highwaymen and highwaywomen have maintained a prominent and sympathetic place in popular culture. Even during the height of the era when highwaymen were most active, their stories were fictionalised and exaggerated.

One good example of this is the fictionalised account of highwayman Dick Turpin’s overnight ride from London to York, an event that most historians believe never actually happened. Highwaymen made an appearance in the works of Shakespeare, and were immortalised in ballads, operas, novels and campside stories.

Perhaps the most famous legacy of the age of highwaymen is the famous legend of Robin Hood, a tale that has become synonymous with both historical Britain and British folk stories.

From charming gentlemen thieves to rebel heiresses, the tales of highwaymen and highwaywomen have captured the imagination of the British population for generations. They have been immortalised in literature, poetry, music and folklore and have become a representation of the rebel spirit.