Middleham Castle was built by Robert Fitzrandolph, 3rd Lord of Middleham and Spennithorne, with work commencing in 1170AD. It replaced an earlier wooden motte and bailey castle that had been built shortly after the Norman Conquest to protect the road from Richmond to Skipton. The new stone keep was one of the largest in England, with walls 3.7 metres thick.

In 1270AD, Middleham Castle passed into the hands of the Neville family. Around 1300AD, Ralph Neville enlarged the castle, encompassing the keep with a high curtain wall.

When Richard, Duke of York, was killed at the Battle of Wakefield during The War of the Roses in December 1460AD, his sons (George, Duke of Clarence, and Richard, Duke of Gloucester - who would later be crowned Richard III) passed into the care of Richard Neville, 16th Earl of Warwick ("Kingmaker"), who raised them at Middleham Castle with his own family.

Once Richard ascended to the throne as Richard III in 1483AD, he spent little time at Middleham Castle during his brief reign. Following his death at The Battle of Bosworth in 1485AD, the castle remained crown property until it was sold by James I to Sir Henry Linley in 1604AD. Henry carried out some repairs, and made the castle his residence until his death in 1610AD. It was occupied by his descendants until 1644AD, when it served as a prison and a garrison during the English Civil War. In 1646AD, Parliament ordered the slighting of the castle, and the eastern wall was destroyed, preventing any further defensive use. Subsequently, Middleham Castle fell into disuse and passed out of the history books.

Today, Middleham Castle survives as an austere and imposing structure. Although it is very ruinous, most of the curtain wall remains intact, and the shell of the keep gives a fair impression of how this fortification must once have looked. The space between the keep and curtain wall is unusually tight, suggesting that the residential function of the castle was more important than the defensive function.