Humphrey Kynaston, Shropshire’s most infamous highwayman


PHILIP DAVIES says little know outlaw Humphrey Kynaston would give Dick Turpin a run for his money!

Humphrey Kynaston

Who was Humphrey Kynaston?

Everyone has heard of Robin Hood: the outlaw turned folk hero who stole from the rich only to give it away to the poor, but this mythical figure dressed in Lincoln green wasn’t just limited to Sherwood forest. Stories of outlaws and highwaymen are littered throughout British folklore, Dick Turpin, Tom Cox, the ladies’ man Claude Duval. Shropshire had its own terror of the highways and much like the aforementioned Robin Hood, he is rumoured to have given everything he stole away to those with greater need than himself. This outlaw was called Humphrey Kynaston and this is his story.

The Devil to Pay

Humphrey was born in 1474 to Sir Roger Kynaston and Lady Elizabeth Grey and grew up in Myddle Castle. Humphrey’s early life was very much one of privilege and much like another Shropshire character, ‘Mad’ Jack Mytton, he was a bit of a hellraiser, in tie earning himself the nickname of ‘Wild’ Humphrey. It was this extravagant and boisterous lifestyle which saw Myddle Castle fall into disrepair. And so, with heavy debts coming due, Humphrey saw fit to leave it.

Whether it was these debts that saw Humphrey turn to highway robbery is unclear, but if it was he certainly didn’t keep all of the money he stole to himself, preferring instead to hand over his ill-gotten gains to the poor and needy in the nearby village of Nesscliffe.

The Devil Rides Out

The life of a highwayman is far from easy and Humphrey soon found himself declared outlaw and hunted by local law enforcement and so, unable to return to his home, he instead lived in a cave that he had found in the cliff faces of Nescliffe. Much like Dick Turpin and Black Bess, Humphrey also kept a horse that was almost as famous as he himself was, although his horse had the slightly more macabre name of Beelzebub.

Beelzebub would live in the cave with Humphrey and the two of them became much beloved by the local people who would feed and tend to the horse on Humphrey’s behalf as well as providing Humphrey himself with food and much needed secrecy.

Chasing the Devil

The local sheriff was charged with capturing Humphrey and there are many stories of narrow escapes and frantic chases. The most famous of concerns the time when the sheriff caught wind of Humphrey’s movements. Humphrey on this particular occasion was a few miles away from his haven in Nesscliffe and, unfortunately for him, he was on the other side of the River Severn. The sheriff sought to press his advantage by having his men remove a few planks from Montford Bridge which was the only crossing point for some distance.

With the trap set the sheriff and his men chased Humphrey, who was of course riding Beelzebub, towards the bridge surmising that with the bridge out of action, Humphrey’s fate was sealed. What the sheriff hadn’t considered was just how agile Humphrey’s steed was and Beelzebub cleared the missing planks with ease, carrying them both away to safety.

Drink with the Devil

Humphrey’s life as a highwayman also gave him a ruthless streak. One night he called into his favourite inn, the Old Three Pigeons, and found a man sat in his seat. Without a thought Humphrey pulled out a pistol and shot the man dead where he sat and subsequently fled the scene of the crime by climbing the chimney and escaping across the roof of the pub.

The pub can still be in Nesscliffe, only a few hundred metres away from the cave itself. Also remaining is Humphrey’s seat next to the fireplace and although Humphrey himself may have died some years ago, it is a brave soul who sits in his chair as there have been numerous stories of ghostly footsteps followed a gunshot often heard within its vicinity!

The Devil his Due

Little is known about Humphrey’s later life. There are rumours he was granted a Royal pardon after he provided Henry VIII with men to fight in France, others that he simply gave up his life of infamy. Rather surprisingly, given his lifestyle, Humphrey left a will and so the year of his death is known to be 1534 as the will itself was proven in January of 1535.

Although we may know when he died, where remains a mystery, once again, rumour and conjecture abound with some sources claiming that he lived comfortably on the estate in Welshpool and it was here that he died, other simply say that it was in the cave he gave his name to that he met his end. Or just maybe it was Beelzebub who, after years of faithful service staked a final claim to Humphrey, body and soul…


  1. Last week, I was in the Three Pigeons Pub on my way to Wild Humphrey’s cave. A gentlemen there claimed that, on a lark, he made up the story of Wild Humphrey’s shooting a man who sat in Humphrey’s chair. You might want to go back to the pub and double-check the veracity of the story.


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