Springing up around the Norman castle built at a strategic point overlooking the River Wye, Chepstow was a major medieval powerhouse. Nowadays, it’s a lively town that combines the best of ancient and modern. It’s also the perfect base for exploring the beautiful Wye Valley. Planning a visit? Here’s are a few things you need to see and do.

Storm the castle

Chepstow’s Great Tower keep was commissioned by William the Conqueror barely a year after the Battle of Hastings, making Chepstow Castle Britain’s oldest surviving post-Roman stone castle. Three major building phases followed. Overlooking the Wye, its position was highly strategic. We don’t mind a bit if you pop across to the English side of the river – the views from there are fantastic.

Hit the high street

Chepstow, which means marketplace in Old English, is still a great place for shoppers. You’ll find plenty of tempting independent boutiques amid the handsome Georgian and Victorian buildings in the centre of town. The town has also received an award-winning redevelopment, adding smart pedestrian areas decorated with stone walls and sculptures inspired by local legends.

Explore the past

On Bridge Street, near the castle, you’ll find Chepstow Museum. This substantial Georgian townhouse is packed with displays revealing the history of Chepstow and the River Wye. You’ll see photos and artefacts relating to fishing, the wine trade and shipbuilding, plus paintings by artists who toured the Wye Valley’s most romantic spots in the 18th and 19th centuries.

Walk the walls

Chepstow’s stone wall, built in the 13th century, used to have a main gate with a portcullis, where toll collectors would extract taxes from anyone bringing merchandise into town. The gate that stands today is a comparative youngster at a measly 500 years old – and you can now stroll through for free, no matter what you’re carrying.

Cross the bridge

This striking Regency road bridge has carried traffic from Chepstow to Gloucestershire since 1816. With massive pillars topped by five arches of gracefully curved cast iron, it crosses one of the world’s most tidal stretches of river. Between high and low tide, the Wye can drop by almost 15 metres.

A landscape image of plants in the foreground and a bridge over the River Wye in the background
White building on the river bank with hills in the background
Chepstow

Go to church

St Mary’s Priory Church is the earliest example of Romanesque architecture in Wales. Founded in the 11th century as part of a Benedictine priory, it’s similar in age to the Norman keep of Chepstow Castle. It’s been altered over the centuries, but the intricately decorated sandstone arch over the west door is unmistakably Norman.

Walk the Wye Valley

From Chepstow Castle car park, a 17-mile waymarked walk meanders all the way to Monmouth via the Lower Wye. You’ll travel through a landscape of wooded gorges and green riverbanks that’s both a Site of Special Scientific Interest and an Area of Outstanding Natural Beauty. It won’t take you long to see just why this are has been attracting visitors for centuries.

Bigsweir Bridge over River Wye
Bigsweir Bridge over River Wye

Go to the races

Are you feeling lucky? Famous as the home of the Welsh National, which takes place each December, Chepstow Racecourse runs thrilling race days throughout the year. It’s also a popular venue for live music and entertainment.

Be inspired by Tintern Abbey

The romantic ruins of Tintern Abbey are less than six miles from the centre of Chepstow by bike, bus or car. Famous for inspiring the poet William Wordsworth, this ruined Cistercian Abbey is still a magical place. For the best views, head for the Offa’s Dyke Path and up to Devil’s Pulpit. According to legend, this rocky outcrop overlooking the Abbey was once used by Satan himself as he tried to tempt the monks in the valley below away from their holy duties.

View at dawn in autumn from south east of Tintern Abbey
Tintern Abbey