The first Castle in the district was at Pont Hendre and was probably built by either Walter de Lacy or his son Roger de Lacy. It was the scene of bitter fighting between Roger Fitzmiles, 2nd Earl of Hereford, Gilbert Talbot and the de Lacys in the Anarchy of 1136 to 1154, during the reign of King Stephen. Gilbert de Lacy won the contest and his second son Hugh de Lacy was recorded as holding this district in 1166. Hugh de Lacy was killed in Ireland in 1186 and the next year two Castles were recorded in this district in the Royal Pipe Rolls. These were Pont Hendre and the recently built Longtown which was described as a new Castle. In 1189 Hugh's son Walter de Lacy was granted Longtown Castle and he was probably responsible for much of the masonry that dominates the town. Walter died greatly in debt to the Crown in 1241 after a very active and varied career. East of the Masonry Castle is a rectangular enclosure which may well be the fortification made by Harold Godwinson in 1056. Harold went on to become King Harold II who was killed at the Battle of Hastings in 1066. It is maintained today by English Heritage.

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