hepstow Castle is situated on the mouth of the river Wye and is a gate-house to the Vale of Wye. Built by William or his son Roger Fitz Osbern on a high cliff overlooking the river the castle was well situated to control movements and as a base for further exploration of Wales. In the early 12th century the castle came into the hands of the de Clare family. When Richard 'Strongbow' de Clare died in 1176 he left a daughter Isabel as heiress. Isabel married William Marshal and the castle remained with the Marshal family until 1245 when the last in the Marshal line died. Chepstow then passed on to Roger Bigod, the fourth Earl of Norfolk.

The castle is built on a thin, steeply sided rocky outcrop overlooking the River Wye. The rear of the castle is defended by a natural ravine. Internally the castle is divided into three separate baileys, an upper, middle and lower bailey following the contours of the rocky foundations it stands upon.