Today Brecon is in Welsh hands, however, it has not always been so. In the distant past there were times when the river Usk, which flows around the town, ran red with the blood of either Welsh, Norman or English dead: as the forces of the 'The Prince of Wales' at the time fought bitter campaigns first to take the town, then attempt to hold it to no avail.

During medieval times the town was encompassed by a wide stone wall with entry being gained by means of four gateways; Struet gate in the north, Watton gate in the east, while from the west it was possible to gain entry by means of two gates in close proximity to each other, Bridgegate and Watergate.

It was the Watergate where as often as not Welsh forces attempted to gain entry, not such a sensible idea when one considers that the “gate” came under both the protection of Norman bowmen high up on the ramparts of the castle of Brecon and those that where situated behind the wall, that ran from the Watergate back across the Honddu river to the Postern gate of the castle.

How did the castle and the one time County market town come to be situated on the confluence of the Usk and Honddu rivers and why? That I shall tell you dear surfer. Also I shall tell you of some of those Welsh Princes that attacked, both the castle and the town, not once but several times in a bid to both defeat and push back those that had invaded my land. Yes Brecon was a bloody town, but it was also well defended.

Hell bent on acquiring for himself the rich pickings of land and plunder that other Norman barons were acquiring on their forays into Wales, Bernard de Newmarch advanced up the Dore valley from his lands at Gromont in Herefordshire. After reaching Hay on Wye, where he constructed a castle and Richard fitz Pons succeeded to it, he continued to advance with his band of well armed Norman knights up the valley of the river Wye. His diversion into the valley of the river Llynfi in 1088 allowed him to venture upon Talgarth the ancient Welsh capital of Brycheiniog. Consolidation of his newly acquired lands, which included building a castle at Bronllys, took two years. However, eager for more spoils, by the later end of 1090 he was advancing west again and in the spring of 1091 reached Brecon. His keen military brain told him that here above the confluence of the heavily wooded valleys of rivers Honddu and Usk was the ideal position upon which to build a castle.

No sooner had the ground been cleared however, than the local Welsh chieftain Bleddyn ap Maenarch and his men struck, but to no avail for the Norman chained mailed knights soon put them to flight and the construction of the prefabricated wooden structure based on the initial one at Hastings in Kent continued. However, determined that the Norman invader should be driven out, Bleddyn called for armed support from his brother in law Rhys ap Tewdwr, the king of Deheubarth. When the two sides met in battle three mile north of Brecon it was the Norman Bernard de Newmarch who emerged the victor. Indeed his chain mailed knights, fighting on horseback with lance, shield, and sword decimated the Welsh allies. This could be seen the following morning by those moaning the dead, for both Bleddyn and Rhys wore the masks of death with great cuts to their bodies and head.

The strength of Brecon continued to grow, soon the castle turned from being a wooded prefabricated structure to that of one of stone with ten tall towers that dominated the local skyline. The defences of the town to were strengthened by a stone wall with entry now being gained by four major gates. In 1217 Llywelyn ap Iorwerth, “Llywelyn The Great” and prince of Gwynedd in north Wales, advanced south and placed the town under siege. However, the townspeople succeeded in buying him off with 100 marks and five hostages. It was a different scenario when Llywelyn again advanced south in 1231, this time there was no placating him. The town was successfully overrun and put to the torch, as for the castle; well that held out

In 1233 Brecon was once again the focus of Llywelyn's attentions, once again his men successfully stormed the walls and fired the town. Even the castle was subjected to a more determined effort, to the point that siege engines were deployed for a whole month in an attempt to break in. However, the immense effort was to no avail, for the walls plus the garrison of the sturdily built fortress repelled all attempts to break in. Following the withdrawal of Llywelyn the citizens of the border town enjoyed twenty years of peace, that was until Llywelyn ap Gruffudd the grandson of “Llywelyn the Great” decided that Brecon was the ideal place from which to launch his attacks on Gilbert de Clare the lord of Glamorgan. Following his capture of the town Llywelyn, at the treaty of Montgomery in 1267, was allowed to retain Brecon, from where in 1270 he launched his successful attack against Caerphilly castle. However, despite this success by the Prince of Wales, the lordship of Brecon was back in English hands by 1273. Any further destruction to the town by Llywelyn was avoided by his untimely death at Builth in December 1282.

For nearly a hundred and twenty years, following the death of Llywelyn, Brecon enjoyed a peaceful existence, traders bought and sold their goods, families were raised and there was a hustle and bustle around the border town. Towards the end of September 1400 that all changed, and it once again became a town at war; for news reached the town that in the north east of Wales all hell had broken loose. Owain Glyndwr had been sworn as the new Prince of Wales and then had risen in revolt and attacked Ruthin castle and town.