Run by Cadw (the Welsh historic monuments agency), magnificent Chepstow Castle perches atop a limestone cliff overhanging the river, guarding the main river crossing from England into South Wales (the best view is from the far bank – cross the 1816 Old Wye Bridge and turn left). It is one of the oldest castles in Britain – building began in 1067, less than a year after William the Conqueror invaded England – and the impressive Great Tower retains its original Norman architecture.
The castle's history is explained in an exhibition in the Lower Bailey, where you can see the oldest surviving castle door in Europe, a massive wooden barrier dated to before 1190. Nearby, beside the stairs down to the wine cellar, take a peek into the latrine and imagine baring your backside over this draughty stone box with a giddy drop straight down to the river. Kids will enjoy the castle grounds – there are plenty of staircases, battlements and wall walks to explore and lots of green space.
A cave in the cliff below the castle is one of many places where legend says King Arthur and his knights are napping until the day they're needed to save Britain.
Once the entire town was enclosed in fortifications, fastening it to the castle. Parts of the 13th-century Port Wall edge the west side of the town centre. You can see it from the Welsh St car park and near the train station. Chepstow's main street, High St, passes through the Gate House , the original city gate, which was restored in the 16th century.
