Along with Rievaulx Abbey, we visited Helmsley Castle. The two are close to each other and have a shared history. Walter l'Espec built the original castle, and also was the one who deeded the land to the Cistercian monks who founded Rievaulx Abbey.
Never really meant to be a serious military fortification, it was more of a manor home to various relations of l'Espec (himself childless), notably his sister who married Peter de Roos, and whose son subsequently updated the castle. It last came to a cousin of de Roos, George Manners, who also updated the structure to the Tudor era. The structures reflect a very long history of ownership and updates to what the then-landholders felt were the fashions and technology of the time.
The castle was never quite breached in battle, but its occupancy ended during the English Civil War when Cromwell's armies besieged the monarchy-loyal occupants. Cromwell's forces were able to prevent relief supplies from reaching the keep, and the loyalists within had to surrender or starve. The surrender was particularly (if cynically) magnanimous, as Cromwell's generals let the loyalists essentially write their own terms -- which included all armsmen to exit the Castle, flintlocks un-saftey'd, and the servants and help of the keep to continue to serve and live. However, after the soldiers, help, and lords/ladies were removed from the Castle, Parliament ordered the castle partly desroyed to prevent anyone from using it again. A huge chunk of the large East tower (the side facing the town, who would no doubt witness the show of Parliament's strength) was set with charges and blown up. It was the only real structural damage the Castle had seen, but it was the end for a long time.
Forgotten and then allowed to fall to ruin, and then used in its ruined state as a fashionable romantic notion of a backdrop by which to have picnics, it came into the care of English Heritage.
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