During the medieval period, multiple river crossings were built on the site of the bridge noted in the Domesday Book to replace others lost to flooding; the current Old Dee Bridge dates from 1353, but at least four other bridges existed on the site beforehand. The bridge became a choke point in Welsh invasions, leading to both ends of the bridge being fitted with sentry posts. Although the bridge formed the only crossing at that point, residents were reluctant to repair the bridge, leading Richard II of England to pay for the crossing to be restored in 1374 "for consideration that as many have been drowned in the water of the Dee since the bridge has been destroyed and broken", being rebuilt with large towers and a drawbridge to further deter Welsh raids.