Female Highwaymen Who Terrorised the English Roads

Why the Roads Looked Like a Man's World

Between roughly 1650 and 1800, the English turnpike road was an unforgiving place to earn a living and a superb place to steal one. Traffic moved in packets: the stagecoach, the post boy, the carrier's wagon, the lone gentleman on a hired hack. Highway robbery was a trade of ambush and bluff. One rider with two pistols, a dark lane and a long stretch of open heath — Hounslow, Bagshot, Finchley Common, Shooters Hill — could stop a coach and be gone before anyone had the nerve to look up.

Women appear in the trial records, but usually at the edges of that trade: as receivers of stolen plate, as lookouts, as the one who quietly sold the watch and the guinea. The woman who rode out herself, pistol in hand and breeches under a riding habit, is rarer than the broadside ballads suggest. She existed all the same, and where the record ran thin, legend filled the gap generously.

One of the best-documented cases is not a robbery at all. Margaret Catchpole, a Suffolk servant, took her master's horse in 1797 and rode it to London, was caught, and was transported to New South Wales. For most women who took to the road, horse theft was the crime and the road was simply the escape route.

Moll Cutpurse: London's Roaring Girl

Mary Frith (c.1584–1659) is the woman most often handed the title. Known across London as Moll Cutpurse, she wore men's clothing as a matter of habit, smoked a pipe, swore fluently and was hauled before the courts in 1611 for dressing indecently. Her public penance at St Paul's Cross drew a crowd, and a stage play, The Roaring Girl, put her on the boards the same year.

Her real business, though, was fencing. She kept a house in Fleet Street, handled stolen goods and knew every cutpurse and housebreaker in the city. Later biographies credit her with holding up the Parliamentarian general Sir Thomas Fairfax on Hounslow Heath — a story that first appears in print some years after her death, and should be treated with the same caution as the rest. The useful lesson is this: in the criminal economy of the period, the woman who handled the goods often made more money than the man who took the risk.

Mary Read and Anne Bonny: Disguise at Sea

These two were pirates rather than highwaymen, but their careers began with the same trick and the same nerve. Mary Read, born in London around 1690, was dressed as a boy by her mother to claim a family allowance, and never entirely gave up the habit: she served aboard a man-of-war, then in a foot regiment in Flanders, before taking ship for the West Indies. Anne Bonny, born in County Cork and raised in Carolina, left her husband in Nassau and joined Calico Jack Rackham's crew.

When Rackham's ship was taken off Jamaica in 1720, the accounts agree that Read and Bonny were the only two who fought, calling on the rest to come up and behave like men while the men hid in the hold. Both pleaded their bellies — that is, pregnancy — and were reprieved. Read died of fever in prison in April 1721; Bonny disappears from the record. Their value to us is practical: they show exactly what the disguise required — clothes, a lowered voice, a remembered swagger and the discipline never to break character.

The Wicked Lady of Markyate: Legend on Watling Street

Katherine Ferrers (1634–1660) of Markyate Cell in Hertfordshire is the great English example of a legend attaching itself to a real place. She married into a Royalist family badly squeezed by the Civil War, and local stories had her slipping out at night in breeches and a mask to rob coaches on the old Roman road of Watling Street, with Nomansland Common as her hunting ground.

The evidence is thin: no indictment, no trial, and her death at twenty-six was recorded as a fall from a horse. Victorian writers, hungry for sensation, added the bricked-up room and the bloodied dress. What the story does preserve accurately is the geography of English highway robbery — a good road, a lonely heath, an inn to vanish into, a gibbet at the crossroads.

What Gave Them Away, and What It Cost Them

• Height and build. An eighteenth-century riding habit — tailored coat, waistcoat and petticoat — already read as masculine at a distance. In the dark, at twenty yards, on a nervous horse, it could pass completely.
• Voice and hands. A high voice or a small hand reaching for a purse was usually what exposed a disguised woman, particularly when a coachman asked her to hand the money over slowly.
• Money and clothes. Most were caught selling the proceeds. Unusual plate or a distinctive watch appearing in a pawnbroker's ledger brought the constable to the door.
• The law. Women could not plead benefit of clergy, and mercy was not the norm. Highway robbery was a capital offence, and the government reward of £40 for a captured highwayman made informers of neighbours.

The punishment was deliberately public: the cart to Tyburn, the crowd, and afterwards the body gibbeted in chains on the very heath where the robberies had happened. That is part of why we remember these women at all. When the crime was rare and the criminal was a woman, the printers knew a story worth selling, and the ballads and Newgate lives gave her a bravado the court records never quite confirm.

Walk Nomansland Common on a raw January afternoon, or follow the old road out past Hounslow, and you can still feel how the trick worked: a bad light, a narrow lane, a cloaked figure on a good horse, and a traveller who would rather hand over a purse than find out who was underneath the hat.