Chepstow is a town and community in Monmouthshire, Wales, adjoining the border with Gloucestershire, England. It is located on the tidal River Wye, about 2 miles above its confluence with the River Severn, and adjoining the western end of the Severn Bridge. It is the easternmost settlement in Wales, situated 16 miles east of Newport, 28 miles east-northeast of Cardiff, 18 miles northwest of Bristol and 110 miles west of London.
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.