Of all the places that call themselves "the gateway to Wales", CHEPSTOW (Cas-Gwent) has probably the greatest claim, situated on the western bank of the River Wye. Chepstow is a sturdy place, robbed of the immediate charm of many other Welsh market towns by soulless modern developments. Nonetheless, there's an identifiably medieval street-plan hemmed in by the thirteenth-century Port Wall, which encases a tight loop of the River Wye and the strategically sited Chepstow Castle (April, May & Oct daily 9.30am–5pm; June– Sept daily 9.30am–6pm; Nov– March Mon– Sat 9.30am–4pm, Sun 11am–4pm; £3.50; Web: www.cadw.wales.gov.uk ). Guarding one of the most important routes into Wales, Chepstow was the first stone castle to be built in Britain. The Lower Ward was the largest of the three enclosures and dates mainly from the thirteenth century. Here you'll find the Great Hall, home to a comprehensive exhibition on the castle's history. Twelfth-century defences separate the Lower Ward from the Middle Ward, which is dominated by the still-imposing ruins of the Great Tower, built in 1067. Beyond this is the far narrower Upper Ward, which leads up to the Barbican watchtower from where there are superb views looking down the cliff to the river estuary.
Opposite is the Chepstow Museum (July– Sept Mon– Sat 10.30am–5.30pm, Sun 2–5pm; Oct– June Mon– Sat 11am–1pm & 2–5pm, Sun 2–5pm; free) containing nostalgic photographs and paintings of the trades supported in the past by the River Wye, and recording Chepstow's brief life in the early twentieth century as a shipbuilding centre.
A mile north of town, Chepstow Racecourse (Tel:01291/622260, Web: www.chepstow-racecourse.co.uk ) is one of the country's premier racing venues, with regular, all-year-round meets. Entrance is off the A466.