Highwaymen emerged in the 17th century to plague travellers on the outskirts of towns and cities. ‘They rob on horseback,’ declared German travel writer Carl Moritz, and ‘terrify travellers, in order to put themselves in possession of their purses.’

Some highwaymen preferred to work alone, a number operated with a partner and others conducted their crimes within a small gang. They typically targeted travellers on horseback, carriages, stagecoaches and the mail coaches. Their earnings could vary considerably. A highwayman might expect to gain a few pence from an impoverished clergyman going about his business but a haul worth thousands of pounds from members of the aristocracy.

These mounted robbers have often been portrayed as gallant, dashing and chivalrous thieves. In fact, many were uncouth, ruthless and desperate felons who enjoyed inflicting violence on their unfortunate victims.

Travellers had, of course, been robbed journeying through England for centuries. However, the development of the pistol and the increase of traffic on the roads offered a tempting new opportunity to the criminally inclined.

Moreover, highwaymen could take advantage of the fact that the country, unlike most of Europe, lacked an effective police force. The poorly trained parish constables and nightwatchmen, responsible for upholding the law, were powerless to prevent the surge in highway robberies.

One of the first recorded highway robbers was a woman. Born Mary Firth in 1584, Moll Cutpurse, as she was known, was the daughter of a reputable London shoemaker. She initially fell into a life of petty crime, but soon gravitated to the more rewarding trade of highway robbery.

Indeed, Moll Cutpurse was so notorious that she had a play, The Roaring Girl, written about her life and she was referenced by Shakespeare in Twelfth Night. Moll, unlike many of her counterparts, evaded justice and died in 1659 at the ripe old age of 75.

Most highway robbers did not have the luxury of dying in their old age. James Hind, for instance, may have been renowned for the generosity and courteousness he displayed towards his victims, but he still went to an early grave in 1652, aged 36.

Hind’s behaviour was imitated by others and contributed to the enduring image of the polite and magnanimous highwayman. A typical example of his conduct occurred when Hind confronted a party of women on the road between Petersfield and Portsmouth. The so-called ‘Grand Thief of England’ apologised profusely for inconveniencing their journey and only took £1,000 of the £3,000 dowry one of the women was carrying as he claimed he had no wish to ruin her marriage.

Some of the earliest highway robbers were gentlemen who lived beyond their means. Walter Tracey, for example, came from a good family and was educated at King’s College, Cambridge. Nevertheless, he quickly discovered that he could not live on the money his father had bequeathed him and resorted to highway robbery to help finance his high living. Tracey was eventually captured when he attempted to rob the Duke of Buckingham in 1634 and was hanged for his misdemeanours at Winchester, aged 38.

The number of highwaymen further increased during the Commonwealth Interregnum (1649–60) when dispossessed officers from the Stuart armies attempted to avenge themselves upon the Roundheads.

Captain Zachary Howard’s insistence on only robbing those connected with the Commonwealth made him one of the most high-profile highwaymen of this period. The most famous of Howard’s exploits was the occasion he stayed at the same Chester inn as Oliver Cromwell and ingratiated himself with the Lord Protector. Cromwell invited his new acquaintance to partake in evening prayers with him but once they had commenced their prayers Howard drew his pistol and proceeded to bound and gag the Lord Protector. Howard escaped with a few valuables, but not before tipping the contents of a chamber pot over Cromwell’s head!

The Restoration of Charles II in 1660 allowed many Cavaliers to reclaim their property and they no longer found it necessary to undertake highway robberies. Those highwaymen who remained were merciless professional felons and highway robbery reached its zenith during the century after Charles II returned to the throne.

‘We are forced to travel, even at noon,’ lamented Horace Walpole, ‘as if we are going into battle.’ Nonetheless, Cesar de Saussure advised travellers not to take matters into their own hands during a hold-up. ‘No one caring to run the risk of being killed or maimed should argue with these highwaymen,’ the Swiss travel writer stated, ‘for were one to make the slightest attempt at self-defence the ruffian would turn bridle and fly, but not before attempting to revenge himself by killing you.’

This warning was sensible advice to travellers. Despite the stereotype of the debonair gentleman thief on horseback, most highwaymen were extremely dangerous and had a proclivity for gratuitous violence. Thomas Wilmot, for instance, was the son of a wealthy squire but his extravagant lifestyle lost him his inheritance, so he took to mounted robbery. Among Wilmot’s unfortunate victims was a wealthy woman who found she was unable remove her diamond ring from her finger and the sadistic miscreant simply cut her finger off.

Dick Turpin is perhaps the most famous highwayman of them all. However, the romantic stories associated with Turpin are the creation of the Victorian novelist William Harrison Ainsworth, who immortalised Turpin and his deeds in his book Rookwood .

Turpin was far removed from the swashbuckling and glamorous figure the novel purports him to be. It is unlikely that he ever owned a horse called Black Bess and it is even less likely that he made his fabled journey, at record speed, from London to York. Turpin, a former butcher from Whitechapel, was a vicious criminal, specialising in burglary before turning to highway robbery with his partner in crime, Tom King. When his confederate was apprehended Turpin escaped to Yorkshire. He squandered the opportunity to start a new life and was arrested for horse stealing. He was subsequently identified as the infamous highwayman and was hanged in York in 1739.

Travellers were certainly not the only victims of highway robberies. In January 1781, for example, the Weston brothers held up a Royal Mail coach and absconded with 35 mailbags with an estimated value of £15,000. Similarly, a gang of seven highwaymen carried out an equally audacious robbery on the Manchester carrier on the road to St Albans in November 1690. The gang succeeded in taking £15,000 in tax money that was headed for London.

Successive governments failed to produce specific policies to curb the growth in highway robberies and it was not until the introduction of the Bow Street Horse Patrol in 1763 that numbers began to decline.

Indeed, the patrol was so successful that the government believed that highwaymen had been permanently removed from the roads and refused to provide any more funding for a scheme they claimed was no longer required. Unsurprisingly, once the patrol was demobilised highwaymen returned to torment travellers. The patrol was reintroduced in 1805 and played a key role in finally ridding the country of the menace it had faced for almost two centuries.

There were several other important factors that account for the eventual disappearance of highwaymen from the roads of England. The expansion of the banking system and the use of cheques meant that travellers no longer carried huge amounts of money on their journey. Furthermore, the improvement of road surfaces increased the pace at which horses could travel. This made them more challenging to stop and enhanced the speed of those in pursuit. Hedges and fences were also being erected on agricultural land and this made it more difficult for highway robbers to flee the scene of their crimes. Moreover, highwaymen could no longer rely on finding safe refuge in an inn or a tavern after Justices of the Peace began to refuse licences to establishments that were rumoured to provide sanctuary. Consequently, the cumulative impact of these measures saw the age of the highwayman gradually draw to a close in the early 19th century. {