Chepstow (Cas-Gwent) is the first Welsh town on the main road into Wales; and as such is a gateway town to Wales. Chepstow means 'market place' or 'ceap stowe' in old English.
A fortified town, much of the town's walls remain, notably, the 13th century Port Wall and the Town Arch. The latter, according to the Argus' Fred Hando, 'survived not only the storms of centuries, but the profanity of the drivers of heavy motor vehicles.' Chepstow Castle is one of Wales' most impressive, both for its stature and location. Built on the cliffs overlooking the river, it stands guard over what was one of the most important routes into Wales. The Castle's Great Hall is home to an exhibition depicting the building's history. The artefacts include suits of armour from the English Civil War. Also open to the public are the Great Tower and the Watch Tower.
Chepstow Museum is opposite the castle, with photos, paintings and artefacts from Chepstow's rich and varied past.
Beaufort Square has many buildings dating back to the 18th and early 19th centuries. Next to the square's War Memorial stands a captured gun from a German First World War submarine, which was presented to Chepstow in recognition of the bravery of Able Seaman Williams V.C, a Chepstow man killed during the landings at Gallipoli.
Leading from The High Street, there is the cast-iron, five-arch bridge, built in 1816 by John Rennie to span the Wye. Leading from the bridge is The Back, or wharf, alongside the river. The Union Jack painted on the English side rockface has been a Chepstow curiosity since 1935 and is regularly repainted.
Chepstow is also home to the famous racecourse which plays host to year round National Hunt and Flat Racing, including the Welsh Grand National.
Acknowledgements: Hando's Gwent, Chris Barber ed. Blorenge Books The Town of Chepstow - Ivor Waters Gwent County Council Guide, 1992