Even today, the mention of the word ‘highwayman’ conjures up a certain image – that of a masked, well-dressed man astride a horse, brandishing a pistol and demanding that rich travellers in a stage-coach ‘stand and deliver’ (in other words, hand over whatever cash and assorted valuables they might have on them) somewhere on an open road at some point in the seventeenth or eighteenth century. Having made off with the loot, he would of course outwit the authorities if they sent anyone after him. It can be a rather romantic image even though the reality was far from romantic – these were brutal, violent men operating in a brutal, violent era.
In a very real sense, there was nothing new about highway robbery even though it only really became a thing in the seventeenth century. Thieves who operated on foot – footpads – had been robbing travellers for as long as there had been roads. However, the gun-toting thief on horseback was something new to the seventeenth century. This was a violent age, and the increased availability and effectiveness of firearms combined with the proliferation of men, often former soldiers, who either lacked or didn’t much care for gainful employment and knew how to use a gun while riding a horse (the latter being vital to ensure a quick getaway). They were helped by the ineptitude of the law enforcement system of the period; in the days before organised policing, the job invariably fell to the parish constable who was usually under-equipped to deal with anything other than minor crime, and who was often thought of as being lazy or incompetent (Shakespeare having set the standard for that particular stereotype with Dogberry in Much Ado About Nothing).
The mounted thieves started to become known as ‘highwaymen’ in the mid-seventeenth century; they were also known as ‘gentlemen of the road’ on account that many of them dressed smartly enough to pass for gentry even if they were of more humble birth. The famous demand to ‘stand and deliver’ goes back to that time, while the earliest references to the follow-up ‘your money or your life’ are from trial reports dating back to the mid-eighteenth century. The growing print industry produced pamphlets detailing their crimes, which brought them to the attention of the public (this would continue in the eighteenth century with publications like the Newgate Calendar and plays like The Beggar’s Opera, followed by the ‘penny dreadfuls’ of the nineteenth century).
One of the earliest highwaymen to become well-known in England was James Hind, who had fought for the Royalists in the Civil War and took to highway robbery during the time of the Protectorate, preying in particular on those associated with the Parliamentarian cause (he once tried, and failed, to rob Oliver Cromwell himself). Others followed, some becoming famous in their time. Claude Duval was a Frenchman who operated just north of Restoration-era London; one of the first highwaymen to dress in fashionable clothes and put on gentlemanly airs, he’s said to have once agreed to only take some of his victim’s money, as opposed to all of it, if the man’s wife agreed to dance with him by the side of the road (which she did). William Nevison was a former soldier who rode from Kent to York in less than a day (a previously unheard-of feat) in order to establish an alibi, a tale that greatly amused Charles II. Robert Congden was an Old Etonian gentleman-farmer by day and a highwayman by night who held up the Earl of Dorset for a thousand guineas.
Most famous of them all, though, was the Essex publican’s son Dick Turpin, who had started out as a butcher before turning to crime; in addition to being a highwayman he was also a poacher, a burglar and, like many of his fellow-highwaymen, a cold-blooded killer. Such was Turpin’s fame that acts performed by other highwaymen, such as Nevison’s ride to York, ended up being attributed to him. Despite their often-violent behaviour some highwaymen – Turpin in particular – were to a degree idolised in that way in which criminals are sometimes, and somehow, made out to be popular heroes (a point picked up in an episode of Blackadder, wherein Baldrick describes a highwayman as “halfway to being the new Robin Hood … he steals from the rich, but he hasn’t got round to giving it to the poor yet”).
From the mid-seventeenth century onwards, the main roads of England became hunting-grounds for the highwaymen and as such very dangerous places – especially the bits that ran through what was then open country on the outskirts of London (although robberies in London itself were not unknown; it was partly concern about highwaymen in Hyde Park that led William III to ensure that Rotten Row, the road between Westminster and Kensington Palace, became the first road in the country to be artificially lit). Highwaymen often chose isolated areas that the main roads passed through; Bagshot Heath, crossed by the roads to both Portsmouth and the West Country, was popular. To the north, Finchley Common on the Great North Road acquired a certain reputation, while to the south on the Dover Road Shooter’s Hill was the venue of choice for hold-ups (it had already got its name from being a place where archery was practiced in the Middle Ages). Many such places had gibbets where the bodies of executed criminals were displayed in metal cages to deter others from a life of crime, and these were well-known to people who often travelled out of London; Samuel Pepys, for example, once mentioned riding past “the man that hangs on Shooter’s Hill”.
Quite a few highwaymen ended up on the gallows, having either been captured in the act or found out later (when people noticed that they’d suddenly started spending a lot more cash than they usually did, for example). Hind was done for treason rather than highway robbery because of his overt support for the Royalist cause, resulting in his being hanged, drawn and quartered. Congden had shot and killed his first victim when he had tried to resist (they really did mean the bit about ‘your money or your life’; robbery and murder both carried the death penalty, back then), while Nevison had killed a constable who’d tried to arrest him; both were hanged for murder. Duval, somewhat unusually it would seem, was actually hanged for no more than highway robbery. Turpin, meanwhile, was arrested for horse theft which was a capital offence at the time – and although some in the government wanted him to stand trial in his native Essex, his trial and subsequent hanging took place at York.
The ‘golden age’ of the highwayman is usually considered as having been the period between the Restoration (1660) and the death of Queen Anne (1714), although Turpin’s ‘career’ post-dates this (he is thought to have turned to crime in the early 1730s, and was hanged in 1739 at the age of 33). Yet there were still some fairly audacious highway robberies being carried out well into the eighteenth century; in 1774, no less a person than the Prime Minister, Lord North, wrote of being “robbed last night as I expected … at the end of Gunnersbury Lane”. For much of the eighteenth century, travellers along England’s roads took to preventative measures – Horace Walpole, the writer (and son of Britain’s first PM), wrote of being “forced to travel, even at noon, as if one was going into battle”. When encountered by two highwaymen outside London, the Duke of Montrose shot and killed one of them (the other escaped, with the duke declining to give pursuit on the grounds that enough blood had already been spilled). The subject of whether or not one should shoot a highwayman, regardless of whether or not he’d shot first, is one that Samuel Johnson (who defined ‘highwayman’ in his Dictionary as simply “a robber that plunders on the publick roads”) had few doubts about. Boswell records that, when it came up in conversation, the great man of letters stated: “I would rather shoot him in the instant when he is attempting to rob me, than afterwards swear against him at the Old-Bailey … I am surer I am right in the one case than in the other. I may be mistaken as to the man, when I swear: I cannot be mistaken, if I shoot him in the act. Besides, we feel less reluctance to take away a man’s life, when we are heated by the injury”. Boswell retorted that Johnson “would rather act from the motive of private passion, than that of publick advantage”, to which Johnson replied: “Nay, Sir, when I shoot the highwayman I act from both.”
In such an atmosphere, it became a matter of routine for coachmen, post-boys and the like to travel either armed or accompanied by someone who was, the weapon of choice usually being a brace of pistols – as guns back then were of the muzzle-loading, single-shot variety it paid to have more than one loaded and ready to fire – or a blunderbuss (an early form of shotgun with a flared muzzle, easier to load while on the move but only effective at close range). Rich travellers, particularly those heading along the Great West Road to the fashionable spa town of Bath, took to travelling with as little money or jewellery in their coaches as possible – the wealth could go on ahead, stuffed in the pockets and saddle-bags of a single servant on horseback, preferably carrying a gun of some sort for his own protection.
Sometimes, a lone rider confronted by a highwayman could get the better of him; one story is of a servant carrying his master’s money who, when confronted by a highwayman, said he’d willingly hand over the cash but asked if the highwayman would be so kind as to put a bullet through his hat first, so that he later could show that he’d put up some sort of resistance before standing and delivering. After the highwayman had obligingly fired, the clever servant produced his own pistol who had been concealed in his coat! As the highwayman had only been armed with a single pistol, the servant now had the advantage and took his opponent to the nearest town to hand him over to the authorities (and, presumably, collect any reward that may have been on offer).
Some highwaymen responded by forming gangs, although many of these were short-lived as they invariably fell out over how to divide the spoils. One of the more notable gangs of highwaymen operated in and around Cherhill, a Wiltshire village on the Great West Road, in the late eighteenth and early nineteenth centuries; being poor men who only owned one set of clothes each (clearly highway robbery was not always lucrative), they became (in)famous for doing their robberies naked so that no-one would be able to identify them by their clothes.
Highway robbery in England died out in the early nineteenth century. Some would assume that it was killed off by the railways, but it would appear there were a number of factors at play. Highway robbery had actually become quite rare by the time that century began, and the last recorded one took place in 1831 (two years after Stephenson built his Rocket). The increase in the turnpike system with its tolled and gated roads had combined in the mid-to-late eighteenth century with the increased enclosure of farmland to limit highwaymen’s activities (there was, quite simply, less open space), and in the early nineteenth century they were limited further by the expansion of cities (especially London) into what had been open countryside. As the cities grew, policing became more effective, and the increased use of banknotes helped too as they were easier to trace than gold coins. The ‘gentleman of the road’ had had his day.