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The site of this pub was occupied by two separate shops, built in Georgian times or possibly earlier. From at least 1851 to 1884, number nine was occupied by Richard Hawkesford, 'ironmonger, bellhanger and nailer'.
The historic walled town of Chepstow is situated in the southeast corner of Wales, at the mouth of the picturesque River Wye - which, at this point, forms the border between Wales and England. The river has played a major part in the commercial life of Chepstow - which once had a bustling port and its own ship-building industry. More recently, the town has become known for its racecourse, developed in the 1920s. The highlight of Chepstow's racing calendar is the Welsh Grand National, staged each year - soon after Christmas.