The Old Wye Bridge was built in 1816 to replace a succession of earlier crossings and remained the primary road bridge between Chepstow and Tutshill (on the English bank) until a modern bridge was constructed nearby in 1988. It is a handsome five-arched structure of local sandstone, and its midpoint is the actual England-Wales border — the River Wye forms the boundary at this stretch. Standing on the bridge gives a clear view up the gorge toward the castle, which rises above the cliff face to the west.
The earlier crossings here were of considerable strategic importance: whoever controlled the crossing at Chepstow controlled the main entry into South Wales. Before the bridge, a ferry operated at this point for centuries. The current bridge is now pedestrian and cycle only, making it a pleasant way to cross between the two countries while taking in the river scenery. The Wye Valley Walk passes over it, and the view downstream toward the railway bridge is worth pausing for.