
Richard II, Conwy Castle, and the Ambush!
- Morgan Ditchburn
- Aug 16
- 5 min read
One of the questions I am often asked on my tours of Conwy is: who was the last monarch to stay at Conwy Castle?
The answer is: the unfortunate Richard II.
His final visit to Conwy took place in August 1399, during a dramatic episode in the political history of medieval England and Wales. Within a matter of weeks, Richard would lose his crown, Henry Bolingbroke would become Henry IV, and the course of English history would change.
What makes the story particularly fascinating is that part of it unfolded not in some distant royal court, but here in North Wales, around Conwy, Colwyn Bay, and Old Colwyn.
And it began with a promise that there would be 'no deceit'.
Yeah right...
Richard II at Conwy
By the summer of 1399, Richard II's position was becoming increasingly precarious.
Richard had become king in 1377, following the death of his grandfather, Edward III. His reign had been turbulent, marked by conflicts with his political opponents and growing concerns about the way he exercised royal authority.
His greatest immediate problem in 1399 was Henry Bolingbroke, the son of John of Gaunt.
Bolingbroke had been exiled from England by Richard. When John of Gaunt died in February 1399, Richard confiscated the extensive estates that should have passed to Bolingbroke.
Bolingbroke responded by returning to England.
What had apparently begun as a dispute over inheritance rapidly developed into something much more dangerous for Richard: a rebellion.
While Bolingbroke gathered support in England, Richard was in Ireland, where he was conducting a military campaign.
He returned to Britain and landed in Wales in July 1399.
By this point, the political situation had deteriorated badly.
Richard made his way across North Wales and eventually reached Conwy Castle.
The great Conwy Castle had been built by Edward I at the end of the thirteenth century and was still a formidable royal stronghold. Richard's presence there was therefore perfectly logical.
But Conwy was not going to provide him with the refuge he needed.
Northumberland Arrives
One of the men involved in the unfolding crisis was Henry Percy, Earl of Northumberland.
Percy was a powerful northern nobleman and had initially been associated with Richard's government. By 1399, however, he had thrown his support behind Bolingbroke.
Northumberland travelled to North Wales and attempted to persuade Richard to leave Conwy and negotiate.
Richard was understandably suspicious.
He had good reason to be.
He was already in a precarious position, and the man asking him to leave the safety of his castle was now aligned with his enemy.
According to the contemporary account of the French chronicler Jean Creton, Northumberland therefore made a solemn promise.
He swore upon the consecrated Host that he intended 'no deceit' towards the king.
Richard apparently accepted the assurance.
And that decision would have disastrous consequences.
The Journey from Conwy
The arrangement was that Northumberland would ride ahead to Rhuddlan Castle.
He would apparently arrange provisions and prepare dinner for Richard's arrival.
Richard would follow behind with a relatively small household.
The king therefore left the security of Conwy Castle on 15 August 1399.
His party consisted of only around twenty-three people.
It must have been a strange journey.
Richard was still king of England, but his authority was rapidly evaporating around him. He was travelling through a landscape in which powerful nobles were choosing sides, and he was placing himself in the hands of a man whose loyalty was, at best, questionable.
The route took him eastwards towards Rhuddlan.
Then came the crucial moment.
The Ambush at Penmaenhead
When Richard's party reached Penmaenhead, Old Colwyn, (although there is some debate as to the exact location this took place - it definitely seems to have been at Colwyn Bay/Old Colwyn) the reality of Northumberland's intentions became clear.
The forces waiting for Richard were not a welcoming party.
They were an armed force.
The king had been trapped.
The promise of 'no deceit' had proved worthless.
Richard was now effectively a prisoner.
It is difficult to overstate how dramatic this moment was.
Only days earlier, Richard II had been occupying one of the greatest castles in Edward I's North Wales.
Now he was being escorted under guard.
Today, thousands of people travel through the area without necessarily realising that a king of England was ambushed nearby!
Flint Castle
Richard was taken to Flint Castle, another of Edward I's great Welsh fortresses.
There, Henry Bolingbroke arrived with his forces.
The contrast could hardly have been greater.
Richard was still technically king.
Bolingbroke was still technically a subject.
But military and political reality was now firmly on Bolingbroke's side.
Richard was subsequently taken from Flint towards Chester.
From there, his fate was effectively sealed.
His reign was coming to an end.
The Fall of Richard II
Richard was eventually forced to abdicate.
On 29 September 1399, he formally surrendered the crown.
The following day, Henry Bolingbroke was proclaimed king as Henry IV.
The speed with which Richard's position collapsed is remarkable.
In July, he had returned to England and Wales as king.
In August, he had left Conwy and been captured.
By the end of September, he had lost his crown.
The deposition of Richard II was a momentous event.
It established a new royal dynasty - the House of Lancaster - and demonstrated that a reigning monarch could be removed from the throne.
It would also have profound consequences for English politics over the following decades.
What Happened to Richard?
Richard did not simply disappear after his deposition.
He was kept in captivity at various locations before eventually being taken to Pontefract Castle in Yorkshire.
There, around 14 February 1400, he died.
Exactly what happened remains a mystery.
One contemporary tradition suggested that Richard was deliberately starved to death.
Other accounts have been interpreted as suggesting that he voluntarily refused food.
Later stories went further and claimed that he was murdered.
The exact circumstances remain uncertain, and the dramatic story of Richard's death has been debated by historians ever since.
His body was initially buried at King's Langley before eventually being moved to Westminster Abbey by Henry V.
One particularly fascinating source for the events is the chronicle of Jean Creton, a French poet and chronicler who was associated with Richard's court.
Creton's account provides a detailed narrative of Richard's final months and includes illustrations of some of the events.
The manuscript is now held by the British Library as Harley MS 1319 and it has some fantastic imagery.
It gives us a remarkable visual glimpse into the crisis surrounding Richard's downfall
A Forgotten Episode in Local History?
What fascinates me most about this story is its local connection.
Richard II's downfall is usually told as a story of kings, nobles, castles, and national politics.
We hear about Westminster, Bolingbroke, the Lancastrians, and Richard's imprisonment at Pontefract.
But Conwy and the North Wales coast were part of the story too.
So the next time you're travelling through Old Colwyn and Colwyn Bay, it is worth remembering what happened there more than six centuries ago.
There are several good books about Richard II, if you wish to find out more!




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