The term ‘highwayman’ dates from the early 17th century. However, the ‘golden age’ of highway robbery in England is arguably associated with the years between the Restoration in 1660 and Queen Anne’s death, in 1714.


There was often a romance attached to stories of highwaymen, who travelled on horseback and were often portrayed as gentlemen, socially superior to ‘footpads’ (who were more akin to modern-day muggers).

Images of highwaymen in the popular imagination were stoked by picture stories by artists such as William Hogarth. Perhaps pre-eminent among these tales was the legend of Dick Turpin.

Were there highwaywomen in real life?

Yes, credible records of highwaywomen can be found in the records of county session court trials.

Highwaywomen also appear in The Newgate Calendar, an 18th and 19th-century volume of crime tales once as ubiquitous in English homes as the Bible.

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There are likewise stories in broadside ballads. These were single sheets of cheap paper printed on just one side, whose name underlines the connection to popular story-songs.

At least two ballads from 1640 tell of Susan Higges, who is said to have enjoyed a 20-year career “in mens attire… upon a Gelding stout” before being recognised and executed.

That said, we need to be cautious about believing hearsay, as the story of Katherine Ferrers illustrates.

A Hertfordshire gentlewoman born in 1634, and the heiress to a substantial fortune, Ferrers lost her wealth on account of her teenage husband’s family pilfering her inheritance amidst the turmoil of the English Civil War and its aftermath.

As some stories have it, Ferrers turned to crime, and was suspected to be the ‘Wicked Lady’, a highwaywoman who terrorised Hertfordshire on horseback. Ferrers fit into the popular trope of a person of genteel background and dwindling fortune, who turned to highway robbery to make a living.

17th-century gentlewoman Katherine Ferrers
Rumour has it that 17th-century gentlewoman Katherine Ferrers turned to a life of highway robbery once she lost her fortune. (Image by Alamy)

Ferrers was reputed to have died in 1660 from gunshot wounds received during a robbery. Rumours of her body being found by servants at the manor house of Markyate Cell, on the same night as a bloodied black horse was discovered wandering the grounds, have passed down the generations.

Despite the popular legend, the idea that Ferrers was a highwaywoman is hard to substantiate.

Did highwaywomen really dress as men?

Stories of so-called ‘cross-dressing’ recur in the ballads, and would have been shocking to contemporary readers. Renegade Nell costume designer Tom Pye, who also worked on Gentleman Jack, says that dress at the turn of the 17th and 18th centuries was heavily gendered.

Louisa Harland as highwaywoman Nell Jackson in Disney+'s 'Renegade Nell'
Louisa Harland as highwaywoman Nell Jackson in Disney+'s 'Renegade Nell' (Photo courtesy of Robert Viglasky/Disney+)

“I think it would have been just totally unexpected that a woman would pass as a man,” he tells HistoryExtra. “Nobody would have seen that coming.” As a result, he says, a figure such as Nell “would have passed quite easily” as a man.

What did society think of women who dressed as men?

The ballads suggest both a fascination with cross-dressing and a sense it was a bad thing. Two ballads from 1690, The Female Frollick and The Female Highway Hector, tell of a highwaywoman being sexually assaulted by a male counterpart, a fate portrayed as being down to her transgressive behaviour.

How many highwaywomen were there?

It’s almost impossible to know. All criminals have good reason to be secretive. Add in the stigma that surrounds not conforming to cisgender norms, and it would be surprising if an exact figure will ever be known.


Renegade Nell is streaming now on Disney+