The fertile, low-lying land between the Monnow and Usk rivers was important for easy access into the agricultural lands of South Wales, and in the eleventh century the Norman invaders built a trio of strongholds here to protect their interests. In 1201, Skenfrith, Grosmont and White castles were presented by King John to Hubert de Burgh, who employed sophisticated new ideas on castle design to replace the earlier, square-keeped structures. In 1260, the advancing army of Llywelyn ap Gruffydd began to threaten the king’s supremacy in South Wales, and the three castles were refortified in readiness. Gradually, the castles were adapted as living quarters and royal administration centres, and the only return to military usage came in 1404–05, when Owain Glyndŵr’s army pressed down to Grosmont, only to be defeated by the future King Henry V. The castles slipped into disrepair and were finally sold separately in 1902, the first time since 1138 that the three had fallen out of single ownership.

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