Chepstow is the gateway to Wales, the first town you reach crossing the River Wye from England on the main road into South Wales. The town sits dramatically above a gorge in the Wye — one of the most beautiful river gorges in Britain — and its strategic position made it one of the most important fortified towns in medieval Wales. The castle here, begun by the Normans in 1067 just after the Conquest, is the oldest surviving stone fortification in Britain, predating even the Tower of London, and it stands in remarkable condition above the river gorge.
The old town is compact and pleasant, with a surviving section of town walls and a High Street that still follows its medieval layout. The Parish Church of St Mary contains elements from a Benedictine priory founded at the same time as the castle. But the real draw beyond the castle is the Wye Valley itself: one of the designated Areas of Outstanding Natural Beauty in Wales, with walking trails along both banks of the river, the ruined Tintern Abbey a short drive upstream, and Offa's Dyke Path (which runs the length of the English-Welsh border) passing through town.
Chepstow is well connected by rail and road to Cardiff and Bristol, and makes a natural base for exploring the Wye Valley and the Forest of Dean on the English side of the river.