Bloody, brutal battles and border castles: The secrets of the savage frontier between England and Wales

Bloody, brutal battles and border castles: The secrets of the savage frontier between England and Wales

Bloodshed, battles, barons and brutality – the sleepy hinterland of the Welsh Marches belies a turbulent history. Mark Hillsdon explores the romantic ruins that remember more troubled times

Published: April 11, 2025 at 1:49 pm

Dawn breaks over White Castle in deepest Monmouthshire, the morning light bringing a golden glow to the great stone walls.

To the south lies Chepstow, the gateway to castle country, to the north a great defensive wall of castles, fortresses and citadels, a medieval Maginot Line that has stood guard along the border between England and Wales for more than 900 years.

These are the Welsh Marches, a beautiful, undulating landscape of hills, hidden dips and secluded valleys, dotted with swathes of woodland and criss-crossed by verdant hedgerows. But their tranquility belies a bloody past of borderland skirmishes, family feuds and some of the most brutal battles of the English Civil War.

It’s thought the term ‘March’ comes from the Anglo Saxon ‘mearc’ meaning boundary, and the Welsh Marches cover a wide strip of land stretching up from Monmouthshire, through Herefordshire, Shropshire and the counties of North Wales.

The history of this borderland is a turbulent one, punctuated with violence and rebellion, as a succession of foreign powers attempted to restrain the rebellious Welsh. First came the Romans, with great forts in towns such as Chester, Gloucester and Caerleon, followed by the Anglo-Saxons with Offa’s Dyke, a mighty earthworks that ran for 150 miles along the border, and lastly the Normans, who saw the answer to the problem in castles– and lots of them.

Getty videoChepstow Castle

Sitting pretty on the banks of the River Wye, the importance of Chepstow as a strategic stronghold wasn’t lost on William the Conqueror, who began work on the town’s great stone castle just a year after his victory at Hastings.

Such was its size and strength that it didn’t come under significant attack until the English Civil War when, as the Royalist stronghold in Monmouthshire, it took a Parliamentarian force led by Oliver Cromwell himself to sack it. None of the defenders were spared.

What are the Trilateral Castles?

For every major bastion like Chepstow, the Marches are dotted with the ruins of dozens of smaller castles, including a trio built by the Normans around the Monnow alley. Known as the Trilateral Castles, they filled a break in the natural defences of the Welsh hills, and guarded the road between Herefordshire and Wales.

White Castle is the biggest and best preserved of the three, a deep and murky moat surrounding its six towers that give imperious views out across the Marches. It would once have been resplendent in a coat of white lime wash but, despite this showy façade, the castle still avoided the ravages of siege towers and canons, hence remaining so well preserved today.

Skenfrith Castle - Getty Images

While White Castle proudly takes the high ground, the castle at Skenfrith (above) is less obtrusive, its impressive round keep just about bobbing above the roofs of the village buildings that surround it. Circular keeps were all the rage in the Marches – omitting corners gave archers a better field of vision, leaving attackers with nowhere to hide.

The village is worth a wander, with its pretty cottages, St Bridget’s Church (whose belltower is topped by a huge wooden dovecote) and lunch at the Bell Inn.

Grosmont Castle Getty Images

Nearby, Grosmont is another romantic ruin, besieged in 1405 by the Welsh. Prince Henry, later King Henry V, showed little mercy when he arrived to relieve the castle, putting over 1,000 Welshmen to the sword.

Ruins of the famous Raglan Castle. Getty Images

Further south is Raglan Castle, an impressive bastion built in the 1430s, a late arrival to the castle-building scene. Despite being intended for show rather than warfare, it held off Cromwell’s forces for
13 weeks in the final sieges of the Civil War, before finally succumbing. It remains an impressive sight today.

Continuing north through the Golden Valley, you sense that crossing the border into England today is far easier than in Norman times. The valley follows the River Dore and takes you through lush farming country and idyllic hamlets but as ever in the Marches, a bloody tale, or a glimpse of the menacing Black Mountains, soon brings back that sense of foreboding.

In the north of Herefordshire sits Mortimer Country, an area inextricably linked with the violent, all-powerful clan that for the first half of the past millennium ruled the area with a mixture of arrogance and avarice. Their power base was Wigmore Castle, the jewel in Mortimer Country’s crown, a tumbledown ruin high on a hill, overgrown and prickly with atmosphere.

Wigmore Castle. Getty Images

The Mortimers took control of the castle in 1075, after the previous owner Roger de Breteuil fell foul of King William. They became one of England’s most powerful families and it’s here that Roger Mortimer probably plotted with his lover, Queen Isabella, to dispose of her husband, Edward II. The king was murdered in 1327 and Mortimer briefly became ruler of England.

The castle is also linked to the battle of Mortimer’s Cross, one of the most brutal battles of the War of the Roses, which in 1461 left the surrounding fields littered with bodies. The battle was preceded by the appearance of the parhelion, a phenomenon when three suns seem to be rising at once. The superstitious soldiers garrisoned at Wigmore were spooked, but Edward, Earl of March (later that year crowned Edward IV) rallied his Yorkist troops, convincing them that it was the sign of the Holy Trinity and that God was on their side. It spurred them on to rout the Lancastrian army.

High up on a spur on the River Clun, Clun Castle is another rambling ruin embroiled in yet more Marchland treachery and intrigue. King John was forced to besiege the castle in 1216 in order to wrestle back control from a wayward feudal baron, John Fitzalan. In the end, money changed hands and the castle stayed in the Fitzalan family on and off for the next 400 years, and proved an important garrison in helping put down Owain Glyndwr’s revolt in the early 1400s.

By the 14th century, the drafty, cold fortress had been turned into a hunting lodge that was considered the height of luxury by medieval standards. In Clun itself, you’ll find a 13th-century packhorse bridge, and the grave of former resident and bad boy playwright John Osborne.

Hopton castle. Getty Images

Perhaps the bloodiest of Mortimer Country’s castles is Hopton, although this sturdy stone edifice is more of a medieval tower house than true fortress. It was saved and restored by the local community and a clearer history of its violent past emerged.

In 1644, a small band of Parliamentarians were besieged inside the tower for over five weeks. When they finally surrendered, they left the safety of the castle expecting to be taken prisoner but were savagely butchered instead, their bodies dumped in a nearby pit.

One of their leaders, Samuel More, survived to write an account of the siege and recalls how: “Presently all the rest being 28 were killed with clubs and such things, after they were stripped naked.” Even on a warm autumnal day, as you stand among the original earthworks dug by the entrenched Royalists, those words bring a chill.

Beyond Hopton, castle country continues, past the fortified manor house at Stokesay, on towards Chirk, another Mortimer family redoubt, and finally the strongholds at Denbigh and Rhuddlan. Sometimes violent, always intriguing, the rich history of the Welsh Marches is still writ large in the castles that dominate the landscape.

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