In the market town of Helmsley in North Yorkshire, a partially destroyed tower peeps out above neat rows of terracotta roofs. To a passer by, the ruins could be just another victim of age-related decay. But, actually, the destruction is lingering damage from a siege by Parliamentarian troops in 1644. Constructed in 1120, Helmsley Castle has plenty of stories to tell.
EARLY DAYS
Helmsley Castle began as a wooden structure built by Walter Espec, who also constructed the nearby Rievaulx Abbey. Walter was childless, so upon his passing, the castle passed to his nephew, Robert de Roos’. In 1186, Robert converted moremuch of the property from timber to stone – it’s his work that we see remaining today.
This was the most influential architectural shift Helmsley Castle underwent, although the generations of the de Roos family would each add their own stamp in the centuries to come.

In 1227, William de Roos built a chapel in the grounds. And in 1258, another Robert de Roos constructed a grand hall and kitchen, transforming the castle grounds into a more residential and sociable property.
In 1464 the family briefly lost possession of Helmsley Castle. Thomas de Roos met a grisly end following his siding with Lancashire after the War of the Roses, and the castle became the property of the Crown.
The castle was reinstated to the family by Henry VII in 1485, albeit not for long since Edmund de Roos was childless. The late 15th century was a prominent time in Helmsley Castle’s story, and the shift in ownership marked huge architectural changes, too. The Manners family took over, and by 1543, many of the major features had been adjusted to accommodate a more residential purpose and Tudor style.
THE CIVIL WAR AND FALL FROM GRACE
Up until the mid-17th century, Helmsley Castle had been spared the brunt of most conflicts. While chaos unravelled around it, the property’s architecture and condition remained largely unscathed. However, in 1644, that changed entirely.
The English Civil War erupted in 1642 when King Charles I raised an army against the English Parliament. The result was a splintering of loyalties across the country, dividing Royalists and Parliamentarians. And, when the Parliamentary army, led by Sir Thomas Fairfax, took the city of York, Royalist strongholds in North Yorkshire became targets.
At this time, George Villiers had just inherited Helmsley Castle in 1632, and as the Duke of Buckingham, he was firmly a Royalist. It was because of these loyalties that, in the autumn of 1644, Parliamentarians launched a three-month siege on the castle. It would be the first time in 500 years that anyone had tested Helmsley’s military defences.

With Villiers exiled to France for his political stance, Sir Jordan Crosland stepped up to lead the military defence of the castle. Amazingly, with just 200 soldiers, the Royalist stronghold held fast to match the 1000 Parliamentarians gathered on foot and on horseback outside. Remarkably, both parties only suffered two casualties during the three months of the siege.
However, around November, dwindling food supplies forced the occupied garrison to surrender. Sir Jordan Crosland marched out alongside his men to surrender to the honourable sound of beating drums underneath flying flags. While the Royalist men were met with mercy, Helmsley Castle was not. To destroy any chance of further military use, the Parliamentarians destroyed the castle’s east side – simultaneously sending an ominous warning to the inhabitants of the nearby town.
While Helmsley Castle would eventually return to the possession of the Villiers family and later to a line of Duncombes, it was never restored to its former glory. The scars you see today are exactly as they were left in the winter of 1644, as if the impact of the Civil War is frozen in time.
VISITING TODAY
Helmsley Castle is now managed by English Heritage and is open daily from 10am until 5pm for visitors to explore its grounds. It’s easy to spend two to three hours walking between the old buildings and admiring the remaining architecture.
The west side remains in much better shape, and entering through the old archway, now shrouded in green ivy, the contrast between the east and west is immediately apparent. The chapel remains are nearly non-existent, and the East Tower cuts a crumbling image. With the help of the audio guide, you piece together bits of the rubble, mentally reconstructing features like the hall and chapel to their heyday.

The Tudor mansion still stands and gardenoffers respite from grisly weather, especially in winter. The exhibitions inside contain a mixture of artifacts, including Civil War weapons like arrows and unexploded mortar bombs.
It’s fascinating to walk through the tactically destroyed ruins and learn about the 900 years of stories. If you take a closer look, Helmsley Castle wears its history on its sleeve.