10 Reasons to Visit Historic Chepstow

The dynamic town of Chepstow sits just by the River Wye in Monmouthshire, South Wales. With a vibrant and varied history dating back to Medieval times, there’s plenty to do here whether you’re after a fun family day out or a relaxing weekend trip for couples.

If you’ve never been to the area before and you’re not sure where to start, you’re in the right place. From historic landmarks to waterside walks and kid-friendly attractions, here are some of our favourite reasons to visit historic Chepstow.

Things to do in Chepstow

1.    Chepstow Castle

Commissioned less than a year after the Battle of Hastings, Chepstow Castle was first built in 1067, making it Britain’s oldest post-Roman stone castle still standing. With a highly strategic position overlooking the River Wye, Chepstow Castle was a great place to stay throughout history, and is certainly a great place to visit now!

Stretching out along the limestone cliff that runs above the River Wye, the castle is home to over six hundred years of history, and visitors can see the evolution of powerful and wealthy Welsh aristocrats from the Tudor and medieval period. The Great Tower keep, which was the first part to be built, is also a must-see!

2.    Chepstow shopping

With a variety of independent boutiques housed in the Georgian and Victorian buildings that make up the town centre, Chepstow is an ideal place for shopaholics. The name of the town even means marketplace in Old English!

A recent award-winning redevelopment also added pedestrianised areas with stone walls and sculptures inspired by local legends, so it’s definitely worth a stroll through the shopping district for this reason alone.

3.    Chepstow Museum

Not far from the castle is Chepstow Museum. Within the walls of this Georgian townhouse are centuries of Welsh history, specifically that of Chepstow itself and the River Wye. Explore local artefacts relating to the wine trade, fishing and shipbuilding, as well as paintings by artists who toured the Wye Valley’s most romantic spots in the 18th and 19th centuries. Whatever your interests, you’ll learn all about Chepstow’s history here.

4.    Chepstow Port Wall

Built in the 1200s, Chepstow Port Wall was used for both defence and to collect taxes from anyone bringing their merchandise to sell in the town. The current gate is much smaller in comparison, having been rebuilt several times over the years, but several sections of the original walls are still intact. Better still, you will no longer have to pay a tax to come through!

5.    St Mary’s Priory Church

For fans of architecture, the earliest example of Romanesque architecture to be found in Wales is St Mary’s Priory Church. Founded in the 11th century as part of a Benedictine priory, it is a similar age to Chepstow Castle’s Norman Keep. Of course, it’s been altered over the centuries, but those in the know will spot that the west door’s intricately decorated sandstone arch clearly dates back to Medieval times.

6.    Walk the Wye Valley

If natural landmarks are more your thing, exploring the nearby Wye Valley has got to be one of the best things to do in Chepstow. With wooded gorges and riverside walks, this Area of Outstanding Natural Beauty is well worth a visit. There are several short walks you can take from Chepstow along the river, or if you’re feeling fit, why not try the seventeen-mile route that takes you all the way to Monmouth via the Lower Wye?

The Wye Valley is also a Site of Special Scientific Interest, so there’s lots for kids to spot along the way. Keep an eye out for otters and red squirrels in particular!  It’s certainly not hard to see why people have been making this journey for centuries.

7.    Chepstow racecourse

The famed home of the Welsh Grand National, Chepstow Racecourse is not just exciting in December! With thrilling race days throughout the year, the racecourse is a great place to visit if you’re feeling lucky or just want something fun to do with your other half during your trip. Plus, if you’re looking for evening entertainment, the racecourse is also a popular venue for live music.

8.    The Cute Farm Experience

Based at a working farm, The Cute Farm Experience sits between Chepstow and Monmouth. The location is stunning, and the owners like to claim it as ‘the most picturesque “office”’ in Wales! Part of what makes the Cute Farm Experience so exciting is the Usk Valley Alpacas that you can actually take for a walk! This alpaca breeding business also breeds blacknose sheep and Mediterranean miniature donkeys that you can pet. There are a variety of tailor-made farm experiences on offer, so if you love cute creatures, this place is definitely worth a visit!

9.    The National Diving & Activity Centre

Looking for fun things to do in Chepstow? This flooded quarry offers some of the best inland diving conditions in Europe. With many attractions on offer, this is a great stop for those with adventurous spirits!  A BAE Aircraft, a Saracen Armoured Vehicle, two Wessex Helicopters, a Giant 3G Swing, a 700m Long Zip Wire and Segway Active are all available at The National Diving & Activity Centre.

There’s even on-site accommodation available at the Wooden Wigwam Village if you need a place to stay. And, when you’ve burned through all your energy, there’s a great selection of food and drink waiting for you at the View Cafe Bar.

10.   Tintern Abbey

Less than six miles from the centre of Chepstow are the epic ruins of Tintern Abbey. These ‘beauteous forms’ that so inspired the poet William Wordsworth, are an amazing place to visit if you’re nearby. Legend tells that the Devil’s Pulpit, which boasts some of the best views of the Abbey, was once used by Satan himself when he tried to tempt the monks in the valley below to abandon their holy duties and move over to the dark side.

To learn more about the country’s cultural history, why not check out the best museums and attractions in Wales? Or, to get closer to nature during your visit to Chepstow, how about booking a stunning spot at a campsite in the Wye Valley? You won’t regret it!