On the Welsh border with England lies the charming town of Chepstow. On its way to the Severn Estuary, the River Wye flows through the town, crossed by the Old Wye Bridge.

Named by the Normans as Striguil after a bend in the river, Chepstow has seen continuous human occupation from the Mesolithic period of around 5000 BCE. Many relics dating from this period can be seen in the town’s museum.

The Sunday Times gave Chepstow its coveted Best Places to Live award. With the beautiful castle, picturesque river and numerous attractions, it’s the perfect holiday destination. Its proximity to Newport makes it the perfect base to explore the region.

Secure the lowest-priced fares, and buy your tickets here.

 

1. Explore the fascinating history of Chepstow Castle

Constructed in 1067 by Earl William Fitz Osbern, Chepstow Castle is Britain's oldest stone fortification, strategically positioned overlooking the River Wye to control the main crossing point during the invasion of Wales. Over the following centuries, it was the site of numerous sieges and battles. After the mid-1600s Civil War, it became a barracks and a political prison, holding figures like Charles I. It later fell into ruin, with parts used as a farmyard and even a glass-blowing factory, until it became a popular feature on the late 1700s Wye Tour for the gentry.

Now in the care of Cadw, Chepstow Castle attracts tourists from around the world. Playing host to numerous events and performances throughout the year, you can explore the battlements, towers and more. Head for the gift shop to complete your visit!

Chepstow Castle

 

2. Meet the animals at the Cute Farm Experience

The aptly named Cute Farm Experience really is that - cute, fluffy farm animals for you to fuss over. Offering stunning views across the Black Mountains, the Cute Farm delivers experiences such as walking with alpacas or catching miniature donkeys. Being a working farm, all the animals are impeccably cared for and very much loved.

The farm’s experiences include taking tea with the animals. For something more special, enjoy a bottle of bubbly whilst feeding the fluffies. Help feed your favourite beasts before taking them for a gentle stroll through the gorgeous Welsh countryside.

  • Perfect for family days out, special occasions or if you just fancy cuddling a cute animal.
  • Experiences from £20.00.
  • Cute Farm Experience website.

 

3. Walk the ancient Offa’s Dyke Path

The long-distance route known as Offa’s Dyke runs for around 60 miles, or 90 km and is part of a much longer 177-mile path. One of Britain’s National Trails, Offa’s Dyke attracts walkers from around the world and passes through eight different counties, the Welsh Marches and Bannau Brycheiniog National Park. It also takes walkers through three  Areas of Outstanding Natural Beauty - the Wye Valley, the Dee Valley and the Shropshire Hills.

Crossing wild moorland, ancient woodland and wide open river valleys, the route takes in historic settlements and their attached castles and abbeys.

 

4. Catch Race Day at Chepstow Racecourse

Known as Wales' premier horse racing venue, Chepstow Racecourse hosts around 32 racing fixtures throughout the year, including the prestigious Coral Welsh Grand National in December.

Set in the picturesque grounds of Piercefield Park, a day at the races offers a lively atmosphere, great hospitality, and the excitement of world-class horse racing. The venue also hosts various family fun days and live music events during the summer months.

 

5. Walk the historic Chepstow Wall and Town Trail

Built largely in the late 13th century, the Chepstow Port Wall was a crucial defence for the ancient port. Much of it remains intact, including the impressive 13th-century Town Gate. Visitors can follow the trail markers to discover hidden corners of the town, view the Norman architecture of St Mary’s Priory Church and learn about Chepstow’s history as a major port for shipbuilding and the wine trade.

  • Perfect if you’re a history buff, walker or want to explore the town centre for free.

 

The impressive castle, beautiful river and numerous attractions make Chepstow a favourite destination for many who return year after year.

Plan ahead: Always check the latest train times and connecting bus services using the our journey planner before you travel.

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