One of the most anglicised of all Welsh towns, Chepstow (Cas-Gwent in Welsh, meaning ‘Castle of Gwent’) sits in a hairpin bend of the River Wye – in fact, its Norman name was Striguil, likely taken from the Welsh word ‘ystraigyl’ meaning ‘bend in the river’, before it appropriated the English version from the words ‘ceap’, meaning market and ‘stowe’ meaning place.

Notwithstanding some clumsy modern development, Chepstow is a place of not inconsiderable charm, thanks to its neat medieval layout and a colourful medley of whitewashed cottages and Georgian townhouses spilling down the hill towards the castle.

The castle is without doubt the town’s big draw, and alone makes Chepstow worth a diversion, though there’s plenty more to stick around for – and if you’re tackling one of the three long-distance trails that start (or finish) here, you could do worse than stay overnight and have a gander before setting off.

What to see and do in Chepstow

Chepstow Castle

Perched high above the cliffs, its sides dropping almost sheer into the muddy waters of the River Wye, Chepstow Castle was described by the late, great Jan Morris as ‘like a huge fist of rock at the very gate of Wales’ – and there’s no question it’s a mightily impressive sight.

It also stakes claim to being the oldest surviving stone-built castle in Wales – not a bad boast considering that there are over 100 castles still standing in the country. The Domesday Book records that the first stones were laid here in 1067 by William Fitz Osbern.

Chepstow Castle stakes claim to being the oldest surviving stone-built castle in Wales © Billy Stock, Shutterstock

It makes sense, chronologically at least, to start in the Great Tower, the oldest, and only Norman-built, part of the castle. A vast rectangular hall-like space measuring over 130ft long, it would have originally had an upper and lower floor, as the pair of sawn-off arches – hewn from Purbeck marble and still bearing some beautifully crafted mouldings – would indicate.

The Great Tower aside, the most rewarding part of the castle is the suite of buildings dispersed around the Lower Bailey. Prominent here is the domestic range, comprising the roofless great hall, the heavily restored and minimally refurnished Earl’s Chamber, the kitchen and service passage, and a dank cellar possessed of a finely vaulted ceiling and a window through which wine and barrels of ale would be winched up from the river directly below.

Chepstow Museum

Directly opposite the castle car park, in a handsome cream-coloured Georgian mansion, the Chepstow Museum is a minor delight. Through a series of packed rooms, it recalls the history of the town, with emphasis on the trades that sustained it, including shipbuilding along the Wye.

Housed in a handsome cream-coloured Georgian mansion, Chepstow Museum is a wonderful place to spend the afternoon © Nilfanion, Wikimedia Commons

There’s also reference to the time when the building, unlikely as it seems, functioned as a Red Cross Hospital during World War I and then as a district hospital. Upstairs is a particularly fine series of topographical prints of Chepstow Castle.

Old Wye Bridge

It’s surprising how few people make it to Chepstow’s town centre, most content to push on elsewhere after visiting the castle. This is a shame because there’s enough to warrant a couple of hours’ exploration, starting with the Old Wye Bridge, an elegant, cast-iron specimen built in 1816 by the splendidly named John Urpeth Rastrick, a renowned railway engineer.

The elegant, cast-iron Old Wye Bridge was built in 1816 © Claudio Divizia, Shutterstock

Costing around £17,850 (about £1.2 million in today’s money), the five-arch bridge actually replaced a 500-year-old wooden structure. A cluster of plaques on the wall by the bridge relay all manner of fascinating facts and figures about both the bridge and the river: one contends that of all the iron arch road bridges built before 1830, this is the only one remaining.

St Mary’s Church

Heading back up Bridge Street, you’ll come to St Mary’s Church at the end of Upper Church Street. As with the castle, the church was founded by William Fitz Osbern in 1072, just a few years after the former, as a Benedictine priory. Beyond the superb Norman doorway, with its zig-zag and lozenge-style stonework, the church interior is a relative mish-mash of styles.

Now very much ageing, and in parts crumbling, a number of structural issues currently plague the building and there have even been threats of closure, so its future remains uncertain.

Travel to Chepstow

By car

Chepstow is one of the most easily accessible places in South Wales, thanks to its proximity to both the M4 and M48, the latter crossing the Severn Bridge just a few miles south of town. Chepstow is also reachable from England via the A48, from the direction of Gloucester, and the Old Wye Bridge a little further up the river.

By train

Chepstow’s Grade II-listed railway station – designed by Isambard Kingdom Brunel – is a 5-minute walk from the town centre on Station Road. Its position on the Cheltenham to Maesteg line makes travelling here by train an attractive proposition; trains to Maesteg (via Caldicot, Newport and Cardiff) run more or less hourly, with services in the other direction to Gloucester and Cheltenham Spa also running hourly.

By bus

The bus station is at the top end of town on Thomas Street, just beyond the West Gate, so an even closer walk to the centre. Bus links are excellent, with services to Caldicot (6 daily), Monmouth (10 daily), Newport (10 daily), Tintern (8 daily Mon–Fri, 5 Sat), Trellech (4 daily Mon–Sat), Usk (5 daily Mon–Sat) and Bristol (hourly Mon–Sat, 4 Sun). If travelling to Cardiff, you’ll need to change in Newport.