Highwaywomen, as might be expected, were far less common than their male counterparts but, having said that, they were not unknown – and they could be just as destructive in their own sweet way.
In the main, they operated in conjunction with a male colleague – often as a husband and wife act. For example, Joan Philips had eloped with Edward Bracey in the late 1600s and Joan, being both beautiful and also a “sexual tease”, would lure some silly fellow to a rendezvous on a “promise” of good things to come. But, of course, Edward Bracey was not the promise expected and the fellow would find himself sorely beaten and relieved of any money or items of value. Joan and Edward were arrested and hanged in the April of 1685. 
Another husband and wife team was James and Anne Wilson. She was described thus :- “Though but young, she can wheedle most cunningly, lie confoundedly, drink and smoke everlastingly, whore insatiably and brazen all her actions most impudently”. Sounds like the sort of girl to take home and introduce to granny!
Her husband was a master of disguise and during the course of many robberies, they would cut the girths and bridles of those robbed and tie the victims to trees to be found and released if lucky – but if not, to die. They were both arrested, tried and executed in 1705.
But there are two women whose stories have received considerable notoriety – and also considerable embellishment so that it is difficult to separate truth from myth.
Mary Frith was born in London c. 1584 into a poor, but loving, family. However, she was always headstrong, disrespectful of authority and someone who delighted to flaunt the accepted manners and behaviour of the time. Because of this, she was known as “The Roaring Girl” and for many years she was a pickpocket who earned the nickname “Moll Cutpurse” because she would cut the purses of her victims without their knowing. She also became known in the London underworld as a fence – but one who would sell the stolen goods back to the original owners!
Much later, when she was middle aged, she turned to highway robbery during the time of the English Civil War. But her particular quarry were Parliamentarians since, for some reason, she was an ardent Royalist. It is rumoured that on one occasion, she robbed and wounded Sir Thomas Fairfax, a close associate of Oliver Cromwell.
Soon afterwards, she was captured, tried, sentenced to death but managed to bribe her way out of execution with a payment of £2000 (a colossal sum in those days – £500 was usually good enough!!) Eventually she died of natural causes – dropsy – in 1659 aged approximately 75.
But perhaps the most famous (reputed) highwaywoman – the subject of two films – was Lady Katherine Ferrers, the “Wicked Lady of Markyate Cell”.
In complete contrast to Moll Cutpurse, she was born an aristocrat in May 1634 but, following a series of family deaths, remarriages and the English Civil War during the 1640s, she reluctantly found herself married to the 16 year old Thomas Fanshawe when only 13. The marriage had been “arranged” so as to combine what remained of the fortunes of the royalist supporting Ferrers and Fanshawe families in the aftermath of the war.
The young couple were sent to live at Markyate Cell (near Dunstable) but since Thomas was forever away from home, Katherine – still a young woman but with no chidren to occupy her mind – was bored to death. It is rumoured that she was influenced by a Ralph Chaplin (a farmer by day but highwayman by night) and sought excitement by waylaying individuals travelling along the Watling Street and, later, on Nomansland Common near St Albans.
The story suggests that she left the Cell at night by means of a secret passage; that she was always dressed in a flowing cloak, a three cornered hat and mask, carrying a pistol and mounted on a fine black horse. Many accounts describe various outrages (and even a killing) with and without an accomplice until one day when Katherine held up a wagon carrying valuable booty. Unbeknown to her, the wagon held a hidden guard with shotgun and during the fracas which followed, Katherine was shot and severely wounded. Her horse, knowing the way home, galloped back to Markyate where Katherine was tended by her servants; but to no avail and she died of her wounds.It is further suggested that, as a member of the aristocracy, she would not have been hanged as a common criminal but that she was quietly buried at Ware in June 1660 – aged 26.
There is a rhyme which reads :- “Near the Cell, there is a well; and near the well there is a tree; and ‘neath the tree the treasure be”. But which is the particular tree, and what the treasure is supposed to be remain a mystery. However one of Katherine’s many ghosts has reputedly been seen swinging from a sycamore tree in the grounds. Is this the tree and is there treasure beneath it? Shall we ever know?
Whatever the truth as to whether or not Lady Katherine Ferrers was ever a highwaywoman – and many dispute it – it is a good yarn nonetheless.