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, and 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, and 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.


1. Explore the Fascinating History of Chepstow Castle

Holding the title for the oldest stone fortification in Britain dating from the Roman era, Chepstow Castle was constructed in 1067 by a friend of William the Conqueror, Earl William Fitz Osbern, and looking out over the River Wye. As the Wye’s main crossing point, the castle held a position of strategic importance in the invasion of Wales. 

The following centuries saw Chepstow Castle being the focus of sieges, defensive actions and battles. After the Civil War in the mid-1600s, the castle became a barracks and political prison, holding such notable prisoners as Charles I and Bishop Jeremy Taylor. 

Soon after this, the castle fell into ruin, with various buildings used as a farmyard, and even a glass blowing factory. By the late 1700s, Chepstow Castle featured on the Wye Tour - a tour of the Wye Valley for the gentry, and the first guide book was published. 

Now in the care of Cadw, Chepstow Castle attracts tourists from around the world. Playing host to numerous events and performances throughout the year, visitors can explore the battlements, towers and more, before heading for the gift shop to complete their 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. 

Offering stunning views across the Black Mountains, the Cute Farm delivers experiences, such as walking with alpacas, or cwtching miniature donkeys, and being a working farm, all the animals are impeccably cared for and very much loved. 

The fluffy alpacas love meeting visitors, the gorgeously woolly Blacknose Sheep from the Valais region of Switzerland just adore being tickled, and the Mediterranean Miniature Donkeys will follow you around all day for a carrot and a fuss. 

The farm’s experiences include taking tea with the animals, or for something more special, enjoying 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 the whole family - who doesn’t love fussing a fluffy? This really is a once-in-a-lifetime experience. 

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

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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 is protected as a scheduled monument. If you prefer to cycle the route instead of walk, the local train service has bike spaces available. 

Following the Anglo-Saxon earthworks that run along the border between Wales and England, the trail crosses the border 20 times and passes through 8 different counties, the Welsh Marches and the 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. At Knighton - the halfway point, the Offa’s Dyke interactive display allows you to experience the full length of the Dyke without exerting yourself too much. There’s even the opportunity to relax with a cup of tea in one of the many cafes in Knighton - perfect. 

Chepstow is almost always prefixed by pretty and it’s easy to see why. The impressive castle, beautiful river and numerous attractions make the town a favourite destination for many who return year after year.