Middleham's first Norman castle was probably a timber ringwork on nearby William's Hill, established after the Conquest on land granted to Alan Rufus and his followers. The present stone castle began in the later twelfth century. Its massive great tower, probably built in the 1170s, contained a hall, chambers, chapel, service rooms, and storage within walls designed to communicate lordly power as much as defense. Later owners added a curtain wall, towers, and residential ranges around the keep, creating a substantial center for a northern estate.

In the thirteenth century Middleham passed through Mary fitz Ranulph to the Neville family. The Nevilles expanded their estates and became among the most powerful nobles in northern England. From Middleham and related castles they administered lands, maintained armed followings, arranged marriages, and participated in royal government. Fourteenth- and fifteenth-century building transformed the enclosure into a more comfortable residence, with apartments, kitchens, halls, and service buildings surrounding the older keep. Its architecture reflected the household required to sustain regional political influence.

Richard Neville, earl of Warwick, known as the Kingmaker, used Middleham during the Wars of the Roses. In 1465 the thirteen-year-old Richard, Duke of Gloucester, entered Warwick's household there and spent several formative years learning the skills expected of a great noble. After Warwick rebelled and died in 1471, Richard acquired much of the Neville power in the north and married Anne Neville. Middleham became one of their principal homes and a base for Richard's work as Edward IV's leading royal representative in the region.

Richard and Anne's only son, Edward of Middleham, was born at or closely associated with the castle around 1474 and died there in 1484. By then Richard had become Richard III. The loss of the prince weakened the new dynasty and gave Middleham a poignant place in the king's brief reign. After Richard's death at Bosworth in 1485, the castle returned to Crown control. It remained useful but no longer housed a noble family with the Nevilles' resources, and its residential fabric gradually declined.

Later tenants and officials occupied parts of Middleham, but roofs and interiors disappeared as the complex became ruinous. State guardianship in the twentieth century brought clearance, archaeological study, and conservation. Finds including objects associated with Richard and Anne have deepened understanding of elite life, although many questions about the building sequence remain. Middleham Castle now preserves one of England's largest Norman keeps within later palatial ranges. Its importance rests on both architecture and household history: the rise of the Nevilles, the education of Richard III, and the use of northern lordship to influence the English crown.