There was probably a timber bridge over the River Usk from the time of planning the Norman town. The first record of its poor condition is in the will of Nigel Chepstow who left money for its repair in 1383. The first stone bridge was designed by the famous Welsh bridge builder William Edwards and built soon after 1750. This bridge survived the great floods of 1795 which swept away the River Usk bridge at Caerleon.

Two of the bridge arches were destroyed in 1877 and coracle fishermen helped people cross the river. The Edwards bridge was very steep and narrow and following a fatal accident when a cart driver fell off the bridge was rebuilt and widened in 1836.