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Chepstow is an ancient market town and former port situated on the River Wye (Afon Gwy) a short distance upstream from where the Wye and Severn rivers merge. A Norman castle founded in 1067 stands at the water's edge. A considerable portion of the massive town wall (Port Wall) remains intact as does the Town Gate which provides access from the west. Until the bypass was built a few years ago, access from the east was limited to John Rennie's cast iron 1816 bridge across the river Wye.

The Priory Church of St Mary, was founded in 1071, also by William FitzOsbern. Benedictine monks from Cormeilles in Normandy (Chepstow's twin town) were there until the Dissolution of the Monasteries between 1536 and 1540. Today it serves as Chepstow's parish church.

Chepstow has long served as the access point for the scenic Lower Wye Valley and two long distance walks are accessible from Chepstow: the Offa's Dyke Path and the Wye Valley Walk. Chepstow racecourse is in the grounds of the ruined Piercefield House. A few miles upstream from Chepstow, on the river Wye, are the ruins of the Cistercian Tintern Abbey, founded in 1131.