From the 11th century to today, it’s all about location


THESE DAYS Chepstow seems something of a backwater, quite overlooked by heritage travelers enroute to South Wales, Gloucestershire or The Marches. It wasn’t always so. For centuries, Chepstow was a well-known, important trading town—right in the center of the action.
Chepstow sits at the crossing of the Severn estuary from England into Wales, where the River Wye (with Gloucestershire on the other side) enters the Severn and the Bristol Channel. That’s the most strategically important location for guarding the Welsh border, and controlling access to the River Wye and the interior of Wales. William the Conqueror knew it, and in 1067 his cousin, William FitzOsbern, began what became the first Norman stone castle in the country. History counts the ways the castle has witnessed the intervening centuries.
More recently, however, the building of the new Severn Crossing Bridge and diversion of the M4 several miles to the south diverted even passing trade from the pretty, modest market town—still crowned by Chepstow Castle. Here is a great interlude for a day on your way to somewhere else—conveniently and easily accessible, yet somehow off the proverbial beaten path.

It’s a Straight Drive West


From the airports or London, directions couldn’t be easier: take the M4 motorway west. Follow the Chepstow signs and the M48 across the old Severn Bridge a couple of miles into town. It’s generally two hours and a bit from the M25. If you’d like a more leisurely, interesting drive, drop down at Hungerford onto the A4 and follow the old road to Bath through Marlborough and Avebury, then regain the M4 past Chippenham. By train, head for Chepstow from Paddington Station; look to change in Newport.

A Room for the Night


In the center of Chepstow itself, the Beaufort Hotel and the Castle Hotel are both old-fashioned town inns with comfortable character. Other options abound in the outskirts, or inquire at the TIC for a quaint B&B.

Chepstow’s Crowning Glory


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Now resting off its hinges, the 13th-century oak door shows the wear of the ages.[/caption]

The place to start exploring is the Tourist Information Centre, right in the parking lot courtyard of Chepstow Castle. Find out what’s happening locally, pick up maps and brochures for the town, Monmouthshire and the Wye Valley.
It’s all uphill into the baileys of Chepstow Castle, its ramparts intact after all the centuries. From the inner bailey and keep, views across the town and river valley are spectacular. Enhanced and rebuilt throughout the Middle Ages, Chepstow, like so many fortresses, besieged twice during the Civil War and fell to Parliament in 1648—its last hurrah as a military garrison and residence.
Right across the street from the castle car park, Chepstow Museum’s local history recounts the town’s story from its glory centuries to its gradual growth as a small market town. To the northeast, you can walk the Old Wye cast iron bridge built in 1816 across the Wye into Gloucestershire for great views of the river and looming castle.

Traffic still passes through Chepstow’s 16th-century Town Gate, and much of its Port Wall built in the 1200s remains standing, and, what is often not the case, the town center has plenty of accessible parking. Chepstow’s tidy downtown market squares and alleys hold major High Streets names (such as Boots and Barclays), but also scores of interesting local shops, pubs and restaurants. Visit as well St. Mary’s Priory Church; since the Benedictine priory was dissolved in 1536, its 11th-century church has been the parish church—and retains many Norman features.

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Onward and upward toward the secure keep at the castle’s highest point above the river.[/caption]

Right in the Neighborhood


Just up the river several miles on the A466 to Monmouth, Tintern Abbey is among the most visited monastic ruins in Britain, and has been for centuries. William Wordsworth was singing its praises more than 200 years ago, and rightly so. The wealthy Cistercian foundation sits on the banks of the Wye, the skeleton of its great abbey church and the monastic complex quite complete and carefully tended. Take tea in the valley, or lunch at the Abbey Inn.

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In a sylvan riverside setting, Tintern Abbey is among the most visited monastic ruins in Britain.[/caption]

Move On – In Any Direction


Chepstow is indeed a gateway to Wales. Follow the winding Wye to Symond’s Yat, the book town of Hay-on-Wye and the Brecon Beacons. Or take the M4 West to Cardiff, the coal valleys and across the Welsh coast to St. Davids. A third easy option is to head north to Hereford and the up through the Marches toward Shropshire on the A46. As we know, there’s never a paucity of choices.