The small Monmouthshire town of Chepstow (Welsh: Cas-gwent) stands on the west bank of the River Wye, on the border with English. After the Norman conquest of England, Chepstow was a key location. It was at the lowest bridging point of the River Wye, provided a base from which to advance Norman control into south Wales, and controlled river access to Hereford and the Marches. The magnificent Chepstow Castle, situated on a clifftop above the Wye and its bridge, is often cited as the oldest surviving stone castle in Britain. The castle was established by William FitzOsbern immediately after the Norman conquest, and was extended in later centuries before becoming ruined after the Civil War. A Benedictine priory was also established within the walled town, which was the centre of the Marcher lordship of Striguil. The port of Chepstow became noted in the Middle Ages for its imports of wine, and also became a major centre for the export of timber and bark, from nearby woodland in the Wye valley and Forest of Dean. In the late eighteenth century the town was a focus of early tourism as part of the "Wye Tour," and the tourist industry remains important.

Other important industries included shipbuilding - one of the First World War National Shipyards was established in the town - and heavy engineering, including the prefabrication of bridges and, now, wind turbine towers. Chepstow is also well known for its racecourse, which has hosted the Welsh National each year since 1949. Comprising a magnificent range of images old and new, this book explores the historical development of this fascinating town and its attractive surrounding area.