Think of a highwayman and the image conjured is of a dashing, even noble, criminal who robs the rich, saves damsels in distress and escapes the clutches of evil noblemen.


The image is a wildly romanticised fallacy but continues to transform brutish killers into ‘gentlemen of the road’. This has never been seen better than with the reputation of the 18th-century Dick Turpin

Who was the real Dick Turpin?

Dick Turpin rode a jet-black horse, Black Bess, and made a legendary ride from London to York, covering some 200 miles, in a single day – or so we are told.

Little of Turpin’s story is true. Black Bess didn’t exist, he didn’t make the fabled ride (a 17th-century highwayman, John ‘Swift Nick’ Nevison, did) and he certainly wasn’t a daring, lovable rogue.

He owes his heroic status to William Harrison Ainsworth’s novel Rookwood (1834). The real man – Richard ‘Dick’ Turpin, from the rural Essex village of Hempstead – was a gruff, scowling murderer with a squalid past.

Dick Turpin's early crimes

As a butcher in the 1730s, Dick Turpin began stealing sheep and cattle, bringing him to the attention of the notorious deer-poaching Essex (or Gregory) Gang.

As his association with them increased, Turpin got involved with their signature crime of raiding homes.

The most famous attack took place on 1 February 1735. In Loughton, the home of the elderly Widow Shelley was invaded by five gang members armed with pistols, one of whom might have been Turpin, who threatened to hold her backside over a fire to make her confess where she hid her money.

The attackers made off with £100 and some silver after helping themselves to ale, wine and meat from the pantry. In another raid, Turpin and the gang beat a 70-year-old man with the butt of a pistol, poured a kettle of water over his head and reputedly abused his servants – all for £30.

How did Dick Turpin become a highwayman?

When the law caught up with the Essex Gang, many of them were executed but Turpin got away and turned to a new line of work – highway robbery.

From a cave in Epping Forest, near London, he and another man, Thomas Rowden, held up people as they walked by. The takes weren’t huge, just a few guineas on occasion, but a bounty of £100 was put on their heads.

Turpin had a taste for the life of a highwayman – he went on to team up with well-known criminal Tom King and committed a string of robberies.

Much has been made of this partnership but, in truth, the two weren’t partners for long as, in early 1737, King was mortally wounded in an altercation over a stolen horse. Some accounts claim it was Turpin who fired the fatal shot, by accident.

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How was Dick Turpin caught?

Turpin was now alone. Most of his friends and accomplices were either dead or in prison. Even his wife spent time in jail. In February 1737, he had written a letter to her arranging to meet up, but the authorities had intercepted the letter and prepared an ambush. Turpin found out about the trap and so scarpered, without warning his wife. She was left to be arrested and imprisoned.

Following King’s death, Turpin fled back to Epping Forest. It was there that, on 4 May, he was spotted living rough by a servant named Thomas Morris, who made a foolhardy attempt to apprehend him. Armed with a carbine, Turpin shot and killed Morris.

Changing his name to John Palmer, Turpin absconded to Yorkshire to evade capture – not in a single ride, but on the ferry. His attempts to lay low were futile as he was eventually arrested on 2 October 1738 for shooting a man’s rooster. In custody, it was revealed that he had stolen a number of horses in Yorkshire.

His true identity remained unknown and it took an act of bizarre coincidence to finally seal Turpin’s fate. From his cell, he wrote to his brother-in-law seeking help. But as the letter sat in the Post Office, Turpin’s handwriting was recognised by a man who worked there. It turned out the man had taught Turpin how to write at school.\

How did Dick Turpin die?

Now arrested as Turpin, not Palmer, he was sentenced to death in York. Remaining guilt-free and sanguine to the last, Turpin spent his last days in jovial mood, entertaining visitors in his cell and buying a new frock coat and shoes for his execution.

On the day, 7 April, he was still in fine form. He paid five mourners to follow his procession through York’s streets to the gallows at Knavesmire. Witnesses remarked on how he “behaved himself with amazing assurance” and bowed to the crowds. After a few words with his executioner, a calm and unrepentant Turpin was hanged.

Despite a violent life of crime, people were fascinated with Turpin’s sordid tale, and his reputation and legend grew.


This content first appeared in the April 2015 issue of History Revealed