Chepstow Town Gate was originally the only gate in the 13th century Port Wall, founded by Roger Bigod, earl of Norfolk. The two storey stone gatehouse, was remodelled in the late 15th century and in 1524, the upper storey was made into a prison by Charles Somerset, earl of Worcester. It is now sadly hemmed in and hidden by other buildings and the windows, battlements and internal archways are 19th and 20th century replacements. Nearby is Chepstow Castle and 2 miles south-west is Moynes Court.