In 1468, the castle was part of the estates granted by the Earl of Norfolk to William Herbert, Earl of Pembroke in exchange for lands in the east of England.
Among his movie appearances, he was best known for The Scarlet Letter (1911), Dr. Jekyll and Mr. Hyde (1913), and Ivanhoe (1913), which was filmed on location in Wales.
The last documents were executed on 7 November 1661 and on 9 November 1661 he was sent to Chepstow Castle.
Wintour's Leap is named after Royalist Sir John Wintour who, hotly pursued on his horse by Parliamentary forces, according to local myth survived a leap off the cliff and, landing safely in the Wye below, swam to safety in the nearby Chepstow Castle.
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