Humphrey "Wild" Kynaston, Highwayman

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Humphrey "Wild" Kynaston, Highwayman

Also Known As: "Wild Humphrey Kynaston"
Birthdate: (66)
Birthplace: Marton in Middle, Shropshire, England
Death: May 1534 (66)
Immediate Family:

Son of Sir Roger Kynaston, of Myddle & Hordley and Elizabeth Kynaston
Husband of Margred ferch William and Elsbeth verch Maredudd
Partner of Elsbeth verch Edward
Father of Margred Kynaston; Elsbeth Kynaston; Elen Kynaston; Jane Kynaston; Edward Kynaston and 4 others
Brother of Jane Kynaston; Lancelot Kynaston; Mary Kynaston; Jane Kynaston; Margred Kynaston and 3 others
Half brother of Sir Thomas Kynaston, of Hordley, Sheriff of Shropshire

Occupation: Highwayman
Managed by: Jonathan Evans
Last Updated:

About Humphrey "Wild" Kynaston, Highwayman

Humphrey Kynaston (–1534), aka Wild Humphrey Kynaston, was an English highwayman who operated in the Shropshire area. The son of the High Sheriff of Shropshire, he was convicted for murder in 1491. After being outlawed, he moved into a cave in the area and lived a lifestyle compared to Robin Hood.

Early life

Humphrey was the youngest son of Sir Roger Kynaston (c. 1432/3 – 1495), High Sheriff of Shropshire, thought to have killed Lord Audley at the Battle of Blore Heath, and Roger's second wife, Lady Elizabeth Grey), daughter of Henry Grey, 2nd Earl of Tankerville and Antigone Plantagenet, the legitimized daughter of Humphrey of Lancaster, 1st Duke of Gloucester (son of Henry IV and Mary de Bohun) and second wife Eleanor de Cobham.

Humphrey was raised in Myddle Castle, which Roger had inherited from his first wife Elizabeth Cobham. He received his "wild" nickname from his outrageous lifestyle, which frequently got him into trouble with the law.

Humphrey inherited Myddle Castle from his father, but later allowed the estate to fall into disrepair.

Marriages and Children

He was married at least twice, firstly to Mariona ferch Williamus ap Griffith ap Robin. They had two children:

  1. Edward Kynaston, who died young
  2. Isabella Kynaston

Humphrey later married Isabella ferch Maredudd ap Howell ap Morrice of Oswaldestre (Oswestry), daughter of Maredudd of Glascoed and Thomasina Ireland of Wrexham, Denbighshire. They had six children:

  1. Margaret Kynaston
  2. Edward Kynaston
  3. Thomasina Kynaston
  4. Robert Kynaston
  5. Roger Kynaston
  6. Jana Kynaston

It is further thought that he married Margred ferch William on 4 August 1497, with whom he had another two children:

  1. Elsbeth Kynaston (b. Cochwillian, 1502)
  2. Edward Kynaston of Hordley (born c.1515)

Life of a Highwayman

On 20 December 1491, Kynaston was found guilty for the murder of John Hughes at Stretton, and declared an outlaw by Henry VII. Some time after that, he moved from Myddle castle to a cave in Nesscliffe Rock. Some sources claim that the reason he moved was due to the criminal charges, and others claim that he was outlawed due to debts.

From 1491 to 1518, Kynaston supposedly lived a life that would match the fictional character Robin Hood. It seems he had a reputation for robbing from the rich, and giving to the poor. In return, the locals protected him, and gave him and his horse ('Beelzebub') food. One time, in an attempt to capture Kynaston, the local sheriff removed several planks from Montford Bridge, to keep him from crossing the River Severn, but his horse managed to leap and safely clear the distance. It is also said that he was a regular patron at the Old Three Pigeons tavern in Shropshire, and his original seat is still there. He may have been pardoned by Henry VII in 1493, but some accounts state that in 1513, Humphrey provided 100 men to aid Henry VIII in France, and in return received a royal pardon 3 to 5 years later.


Humphrey left a will dated 1 May 1534, and that will was proved 26 January 1535. While the year of his death is well known, how he died and where are disputed. Some sources claim he lived comfortably in an estate near Welshpool until he died, and others claim he died of illness in his cave.

Kynaston's Cave

Today the cave is known as Kynaston's Cave, and is located at 52°46′1.78″N 2°54′46.09″W. It has two rooms; he lived in one, and stabled Beelzebub in the other.[9] The cave also featured an iron door for an entrance. This iron door is said to later have become the door for Shrewsbury gaol.[9] There is also an engraving in the cave, which reads H.K. 1564. Although this engraving is concluded to be made by Humphrey, he was dead 30 years before the year 1564. However, he did have a Grandson, Humfridus (b.1530) who may have left the inscription.

NOTES on Humphrey Kynaston: Source: Plantagenet Ancestry of Seventeenth-Century Colonists" by David Faris, p 169 Humphrey Kynaston, of Marton in Middle, co. Salop, Constable of Middle Castle, first son by second marriage, was married for the first time to Margred Ferch William, daughter of William ap Griffith ap Robin, and had one son and one daughter. He was married for the second time to Elsbeth Ferch Maredudd ap Hywel (or Elizabeth Kyffin), daughter of Maredudd ap Hywel ap Maurice of Glascoed, ap Ivan Gethyn of Gartheyr, by Tomasin ferch Richard. They had three sons and two daughters. The will of Humphrey Kynaston was dated 1 May 1534 and proved 16 Jan. 1534. Source: Ancestral File of Doughlas Rene McCoy and Family: Humphrey was born abt 1474 in Knoking, Shropshire, England, and died 1534. IGI source birth 1468, Morton, Shropshire, England, father Roger Kynaston, Elizabeth Frey Batch 5025898, source 1553813 Source: John Kensiston and his Descendants, Ms. Byrd Miles. 1960 Humphry was of Middle and Hardley, was the second son of Sir Roger Kynaston. He succeeded his father as Constable of Middle Castle. He married 1st Marrion dau. of William Griffith, and married 2nd Elizabeth, daughter of Meredeth ap Howell, of Oswaldestre. While he was a tenant of Middle Castle he led a "Riotous and dissolute life" and contracted many debts by which he earned the name "Wild Humphrey." He was a divers himself in a cave near Nescliff, which to this day is called Kynaston's Cave. During Kynaston's residence here, several attempts were made to take him in without success: one time when he was over Montford's Bridge, on the side next to Shrewsbury and must return to his cave over the Bridge, the Undersheriff came with considerable company of men, and the bridge being then composed of stone pillars and planks laid pillar to pillar, they took up several planks, left such an opening as they thought no horse could jump over, and laid themselves in ambush for his return. When Humphrey came and was about to enter the bridge, they rose up to apprehend him, which he preceiving, put spurs to his horse, and riding full speed, leapt over the space and escaped. The measure of this leap was afterward marked out upon a gree place on Knocken Heath, in the road between Knocken and Nescliff with an H and K cut into the ground at the beginning and the end of the leap. The letters were almost ell long and were usually repaired by Mr. Knaston of Ryton. After this Humphrey's Cave was never inhabited but went to ruin. Source: Ancestors of Nataniel Littleton, Humphrey Kynaston signed a will on 1 May 1534 in England. Probed 1-16-1535. He died about 1535 in England He was born in England. Source:John Fludd Index: http::// Fludd Bio_Rob_fludd.htm When Sir Roger (Humphrey's father) died, his widow Elizabeth took up residence at Myddle Castle, which Roger possessed through his first wife (who was the widow of Lord Strange, from whom she had inherited it as her dower house in 1449). Althought the title to the Castle was disputed by the Strange family, Humphrey Kynaston (1474 - 1534), her son, seems to have made it his home, even though his manor was at Morton, Shropshire. He had two wives of low parentage, his first wife being Elizabeth, the daughter of Meredity ap Howel ap Morice of Oswestry and the second Mariana the daughter of William Griffith. Both these marriages had Issue. Gough, the antiquarian, whose knowledge of the history of Myddle Castle is undisputed, wrote of Humphy at this time: " who from his dissolute and notorious manner of life was named 'The Wild." At the Assizes held at Stretton on December 20, 1491, it was alleged that Humphrey was concerned with others, in the murder of John Hughes at Stretton. Evidence was given that on the day of the murder, Humphrey Kynaston, Thomas Kynaston and Robert Hopton who were out riding together, came upon John Hughes. Humphrey struck him on the right side of the breast with a lance thus killing him. Whereupon Thomas Kynaston then lifted his sword and struck Hughes on the left side of the head, while Hopton struck him with a bill on the calf of the left leg. A verdict of "Willful murder" was returned on all three men. It transpired that this event and the enormous debts he had contracted y his imprudent activities finally led him to flee from Middle Castle, which he had allowed to fall into ruins, and to take shelter in a cave in the west point of Nesscliffe Rock, called to this day Kynaston's Cave. He was declared an Outlaw by Henry VII in 1491. This cave is spacious and even comfortable, being divided into two rooms by a strong pillar of the rock, upon which is carved 'HK 1564.' One of these apartments was the stall of the outlaw's celebrated horse, which some to this day, believe to have been the devil. This horse was often turned to graze in the neighbouring fields, and would instantly ascent the steps of the cave when his master whistled. In all his deprecatory adventures Humphrey seems to have a regard for some sort of justice. For what he took from the rich he gave freely to the poor, by whom he was much beloved. Most of the adventures ascribed to him, whether probable or improbable, seem to have been more dictated by whim than a desire to plunder. He had a plentiful supply of hay, corn, and other necessaries from the people around, the rich paying him tribute through fear, and the poor from gratitude." He died in 1534 having been pardoned his crimes by Henry VII in 1493. Source: Sheffield Hallam University, Corvey Women Writers 1796-1834: Review of "Old Stories" by Elizabeth Isabella Spence, author of 'A Traveller's Tale," Longman and Co. 1822 The scene of the story contained in the volumes before us are laid in Shropshire, at Kynasaton's Cave, the present abode of an old woman, who shews it as a curiosity to the traveller, and formerly the resort of a famous outlaw, called sir Humphrey Kynaston, a sort of Rob Roy, whose exploits were matter of much sensation and alarm when he lived, about the year 1564. The interest of the tale of Sir Humphrey Kynaston, turns on the person of his wife, Isabel Griffith, (sic: Mariana?) a beautiful girl, the daughter of a farmer, to whom he had been united before the course of dissipation, which, by degrees, led him to a life terminating in his outlawry. On this he retires with his horse to the cave, known by the name of Kynaston's Cave, and there he resides till seized by fatal illness. To attend and endeavour to relieve him from his malady, a woman famed for her skill in simples, is here introduced to him, and proves to be Isabel his wife, whose love for him had survived all his ill-treatment, and in whose arms he dies.

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Humphrey "Wild" Kynaston, Highwayman's Timeline

April 22, 1468
Marton in Middle, Shropshire, England
Age 46
Age 46
Knoking, Shropshire, , England
May 1534
Age 66