A Welsh settlement existed at Rhuddlan long before the coming of the Norman. Indeed in the days of which I tell the countryside around Rhuddlan formed a natural protective barrier for the mountains of Snowdonia, for it was wet marshy land virtually impossible to cross; certainly not by heavy laden wagons needed for war.

Prior to Norman times Rhuddlan was the seat of power for prince Gruffudd ap Llywelyn, who continually plundered English lands. This constant activity brought him into conflict with Earl Harold of Wessex ( King of England at the time of the Norman invasion ). Gruffudd beat a hasty retreat from plundering the area around Wrexham, when Harold was seen to be advancing against him. However, despite it being the middle of winter with deep snow on the ground, Harold continued to pursue Gruffudd as he retreated into his native Wales.

Harold's progress by the way of the Horseshoe Pass high above the town of Llangollen almost caused him to terminate his campaign for the pass was full of wind driven snow and many men and animals lost their lives because of the cold. By now the tracks of the retreating Gruffudd were also lost. However, a chance happening by one of Harold's scouts upon a wind cleared patch of ground in the upper reaches of the river Clwyd, revealed that Gruffudd had passed that way. On reaching the spot, Harold and his men turned north and swept down the Clwyd valley.

In the meantime at Rhuddlan, having received news that Harold was advancing down the valley, Gruffudd began to load his ship at the quay side. It proved to be a damned close run thing, a gust of wind entered the ship's sails to drive it down the river; just as the first of Harold's men appeared on open ground a mile to the north of the castle. Gruffudd and some of his followers may have escaped, but in rage Harold razed Rhuddlan to the ground.

In 1073 there were new occupants at Rhuddlan. A huge Motte and bailey castle had been constructed and it was home to Robert of Rhuddlan, first cousin to Hugh d'Avranches the first Norman Earl of Chester. It was from Rhuddlan that Robert planed and carried out his advances into north Wales. However, he seemingly forgot two things about the north Wales Welsh; they could organize and they could fight. When Hugh eventually succeeded to advance to Anglesey, his army was severely mauled by the Danes who had come ashore to restock their ships. On the retreat the men of the north were ready and waiting. Time and again they attacked the Norman column as they retreated eastward along the shoreline of north Wales. When the column was forced to swing inland, to avoid Penmaenmawr heights, the men of the mountains struck with full force. Very few Norman's returned to Rhuddlan, Robert certainly didn't.

By 1274 Llywelyn ap Gruffudd was prince of Wales. At the same time, having returned from a crusade, Edward Ist had assumed the crown of England. Llywelyn so misjudged the character of the man. Having got the better of Henry III, he thought he could get the better of Edward too; it was to be a disastrous mistake. In 1276 Edward was determined to bring Llywelyn to heel and ordered fighting men and materials to be assembled at Chester, where on July of 1277 he arrived to take command. By the 22nd he was on the move and soon he had established an advanced base at Flint. With the construction of Flint castle set in motion, supported on the seaward side by twenty 25 armed ships of the Cinque ports, Edward then advanced to Rhuddlan.

Within a month, with construction still going on all around him, Llywelyn was forced to capitulate and sign a surrender in the great hall. When men of Llywelyn's army group again placed Rhuddlan under siege late in 1277, the castle was relieved by an English army from Chester under the command of Count Amadeus V of Savoy early the following year. The castle was never put under siege by my countrymen again.