The majority of castles in England have there origins in securing the territory after the Norman Conquest. As William the Conqueror began to methodically take control of England. As ever with William his response to defiance was not subtle or proportionate, he mercilessly Harried The North. Literally burning and laying to waste areas that were rebelling against his fiefdom. Destroying villages, poisoning the earth so they couldn't immediately return and grow crops. The economic and cultural repercussions of this rippled on for decades, if not centuries.
Helmsley was gifted to William's half brother Robert, but there is little evidence of him building a castle. Robert and Robert's son, and his son in turn, all rebelled against the monarch of the time. After the third incident the family had the control of the Helmsley estate taken away from them. It was given to Walter Espec around 1122 and he invested huge amounts of time, money and patronage into the area. And with Walter the first castle with its wooden battlements and bailey is created. And during his lifetime he began constructing the stone version, which you see now.
Helmsley Castle is quite favourably placed. It's on the route north to Durham and the Scottish Borders and the route west to York, the route east to Whitby. There were regular and sometimes quite serious pillaging raids of Scots this far south, so the castle did have a role as a focus for repelling and deterring them. But there was always an element of it providing merely the outward appearance of strength. A Norman Castle, in its prime, was also there to intimidate the local population too. A lot of what Helmsley Castle is, is just exterior show, to display superior status as much as military power.
If Helmsley Castle was ever really tested out as a medieval military stronghold is unclear. But, formidable as its moat and ramparts may look, it had weak points that further developments across them attempted to compensate for. Investigations of the moat indicate some of it had been clay lined, but this was limited and not across the whole of the moat. This makes it look like an early experiment that failed in making it watertight. The full depth of the moat was hence unable to hold water. That said the height, depth and sequence of the ramparts and battlements, built by the De Ros family who succeeded Espec, would in medieval times have made it no push over to capture.
The De Ros family fell fowl of being on the wrong side in the War of the Roses. So the castle and its estates were bought by the Manners family. One of whom subsequently married the infamous toy boy lover of James 1, and rake on the make, Charles Villiers, Ist Duke of Buckingham. It was not until the Civil War with the increased strength of firepower from cannons and guns, that taking a castle such as at Helmsley became possible. It fell to a siege by Fairfax's New Model Army, surrendering in November 1644. The Parliamentarian's made the castle inoperable as a defensive structure. The 2nd Duke of Buckingham, equally as much of a scoundrel as his father, fled the country until the Restoration returned to him his estates. But from then on the castle ruins were increasingly used as aesthetic adornments to a picturesque landscaped view. Particularly once Duncome Park was created in the 18th and 19th centuries.
The final change for Helmsley Castle came in 1932 when it was taken into state ownership. And slowly the ruins were excavated from centuries of neglect, the build up of metres of soil, rubble and refuse were removed to reveal the full foundational outline of what you see today.
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