From Cardiff to Chepstow: Castles, Caves, and a Dog-Friendly Adventure by Train
2 June 2025
Looking for a day out packed with history, legends and jaw-dropping views – but without the hassle of driving? This stunning 13-mile circular walk from Chepstow to Tintern ticks all the boxes. Easily reached by train from Cardiff Central with Transport for Wales, the route takes in everything from mighty castles and ancient woodland to hidden caves, iconic TV locations and medieval abbey ruins. Better still, dogs are welcome on board, so I brought Piper along for the adventure!
🥾 13 Miles
⏱️ 6-7 hours
📈 914m
Starting at Chepstow Castle: A Mighty Fortress Above the Wye
Stepping off the train, the adventure begins almost immediately. Chepstow Castle – one of the oldest surviving stone castles in Britain – towers above the River Wye less than 10 minutes from the station. Founded in 1067 by William fitzOsbern, a close ally of William the Conqueror, the castle has witnessed nearly 1,000 years of history. Its commanding position above the river was no accident; Chepstow was built to control the crossing point and defend the Welsh borders. Today, its impressive walls and massive gatehouse offer a powerful reminder of the medieval world.
Although Piper and I didn’t venture inside on this trip (dogs aren’t allowed inside), even just viewing the castle from outside set the scene for the rest of the journey.
Into the Woods: The Piercefield Walks and The Grotto
The path soon leads into ancient woodland along the Piercefield Walks – an 18th-century landscaped trail designed to show off dramatic views of the Wye Valley. These walks were once considered among the finest examples of ‘picturesque’ landscaping in Britain, attracting artists, writers, and early tourists.
One highlight is The Grotto, a curious stone shelter built into the side of a hill. It was originally created as a romantic feature on the Piercefield estate, offering visitors a shady resting place while they admired the surrounding views. Today it’s a little overgrown but still atmospheric – a reminder of the days when woodland walks were as much about art and drama as they were about exercise.
Giants Cave: Myth and Viewpoint Combined
Continuing through the woods, you come to Giant’s Cave, a small but intriguing cavern set into the limestone cliffs. Legend has it that a giant once lived here, but whether you believe the tale or not, the real magic lies in the view. A short walk through the cave brings you to a wonderful lookout over the Wye – a peaceful, hidden spot perfect for a breather and some photos. Piper particularly loved exploring the cool shade of the cave!
Tintern Abbey: Cistercian Beauty in the Heart of the Valley
Eventually you arrive at the awe-inspiring ruins of Tintern Abbey. Founded in 1131 by Cistercian monks, Tintern was one of the first Cistercian foundations in Britain, and its ruins remain hauntingly beautiful. Even today, the soaring Gothic arches and empty window frames seem almost alive, echoing centuries of worship, labour, and contemplation.
Standing in the valley surrounded by hills, Tintern Abbey feels timeless – a true highlight of the Wye Valley. There’s also a dog-friendly café nearby, where Piper enjoyed a little snack while I had a well-earned coffee.
Crossing the Wireworks Bridge (aka the ‘Sex Education’ Bridge)
After winding your way down to the river, the route crosses the Wireworks Bridge – instantly recognisable to fans of Netflix’s Sex Education. Originally built in 1876 as part of a railway line serving local industry, the bridge later became a tramway before being repurposed for pedestrians and cyclists. Today it makes a charming crossing point over the Wye, leading you from Wales into Gloucestershire.
The Climb to Devil’s Pulpit: Legendary Views
We began the climb towards the most legendary viewpoint of all: the Devil’s Pulpit. The path winds through lush woodland, climbing steadily until you reach the iconic limestone outcrop. According to local folklore, the Devil himself would stand here, trying to tempt the monks of Tintern away from their holy work.
It’s easy to see why this spot was chosen for such a tale – the view is simply spectacular. From the Pulpit, you can gaze straight down over the Abbey ruins, framed by the lush, green valley. It’s one of those moments that truly makes all the effort worth it. Piper seemed impressed too (although she was mainly focused on finding sticks).
Back to Chepstow and Home
The return leg follows the Offa’s Dyke Path, tracing parts of the ancient earthwork built by King Offa of Mercia in the 8th century. Eventually, we crossed the handsome Old Wye Bridge, built in 1816, and made our way back into Chepstow – where a quick stroll led us back to the railway station.
Within minutes, Piper and I were back on a comfortable Transport for Wales train, heading home to Cardiff – tired, muddy, and very, very happy.
Why Travel with Transport for Wales?
Choosing the train made the whole experience so much easier. No parking stress, no long drives, and no need to leave Piper behind – just simple, relaxing travel through beautiful countryside, straight to the start of the trail. Plus, with regular services from Cardiff Central to Chepstow, it’s perfect for spontaneous days out. Even better, you get 2-for-1 entry at both Chepstow Castle and Tintern Abbey when you show a valid train ticket – a great way to make the most of your adventure and support local heritage sites.