Chepstow Castle occupies a spectacular defensive position on vertical cliffs above the River Wye. It has its origin in the early Norman period when William fitzOsbern, Earl of Hereford from 1067, had juristiction over the area, and is the most southerly of a chain of fortifications along the Welsh March. The great tower may have been commissioned by William I during his visit to South Wales in 1081.

The castle remained unaltered until 1189, when it passed by marriage to William Marshal - at that time one of the most powerful men in the country. Marshal remodelled the castle from the early 1190s until his death in 1219. His revolutionary additions and modifications include the construction of a new gatehouse, the creation of the lower and middle bailey defences, the heightening of the upper bailey curtain and a brand new tower in the South West corner. Later, in the thirteenth century, Roger Bigod, the fifth Earl of Norfolk, transformed Chepstow into a palatial stronghold by building a range of accommodation and service rooms. He also created a massive tower at the south-east corner, Marten's Tower, and an extension of the upper storey of the great tower. Considerable repair work was required throughout the Civil War as the Castle was garrisoned on a number of occasions.

There has been a castle on this strategic site overlooking the River Wye since 1067 and it is one of the most impressive castles in Wales. Chepstow Castle was refortified by William Marshall between 1190 and his death in 1219 and then further enhanced by Roger Bigod in the 1270s. The castle was garrisoned during the Glyndwr rebellion and was besieged twice during the English Civil War. Thirteenth century wallpaintings survive depicting shields.

Following the end of the English Civil wars and the restoration of the monarchy, Chepstow Castle served as a garrison and gaol. Marten Tower is named after its most famous prisoner, Henry Marten, who signed the death warrant for Charles I and died in this castle in 1680. Shortly after his death, the garrison was disbanded and the castle fell into decay.

With the rise of modern tourism in the late eighteenth century, the now ruined Chepstow Castle was rediscovered by travellers in search for picturesque Wales. Among the earliest travellers from Germany was Carl Gottlob Kuttner who visited in 1784. Impressed by the history of the castle, its historic prisoners and prime location on the Wye, he very much regretted not having had more time on his hands to stay a bit longer and draw it from all sides. The Breton, Armand-Louis-Bon Maudet, Comte de Penhouet, visited twelve years later and he was overcome by the architecture, history and beautiful surroundings. His busy travel plan did not allow him to stay long either, but he did find enough time in his travel description to praise the services and kindness of Mrs Williams, the resident tourist guide in the employ of the owner of the castle, the Earl of Beaufort.

Sources included:
Turner, R. 2008. Chepstow Castle: CADW
AHRC-funded project 'Journey to the Past: Wales in historic travel writing from France and Germany'. R. Singer (Bangor University) and S. Fielding (RCAHMW), 2017.
Richard Suggett, Painted Temples: Wallpaintings and Rood-screens in Welsh Churches, 1200–1800, (RCAHMW 2021), pp. 88–9, 90.

RCAHMW 2021