Pickering Castle is a good example of a Norman motte-and-bailey castle where the original wooden defences were gradually replaced by stone. The castle was built by William the Conqueror in 1069-70 while he was in the north of England repressing major uprisings against his rule. The castle proved popular with many later kings who used it as a base for hunting in the surrounding forest.

The castle consists of a large motte surrounded by its own ditch and around this are two baileys. King Henry II began the process of rebuilding the castle in stone, when construction of a new curtain wall around the inner bailey was started in 1180. Over the next sixty years the defences of the inner bailey were further developed, including the building of a circular shell keep on top of the motte. By contrast the outer defences remained in timber until the early 14th century, when King Edward II ordered repairs and improvements to the castle that included the construction of a stone curtain wall around the outer bailey.

Surveys in the 1530's describe a castle already falling into decay, and by 1651 the chapel was the only building still roofed and usable. The chapel is still the only surviving roofed building, although it was greatly restored in the early 19th century and reroofed more recently.