Pickering castle was originally a timber and earth motte and bailey castle. It was developed into a stone motte and bailey castle which had a stone shell keep. The current inner ward was originally the bailey and was built between 1180 and 1187. The keep was developed into a stone shell keep sometime during the years 1216 and 1236 along with the chapel, during this time, and there is a reconstruction of the chapel at the site. Between the years 1323 and 1326 there was an outer ward and curtain wall built along with three towers, there were also two ditches, one situated outside of the curtain wall one in the outer ward. After this there was a gatehouse, ovens, hall and the storehouses built. It is situated on the vale of Pickering and has a considerably steep cliff on the West side which would have been a great defensive attribute.
The original structure was built by the Normans under William the Conqueror in 1069–1070. This early building included the large, central mound (the motte), the outer palisades (enclosing the bailey) and internal buildings, notably the keep on top of the motte. Ditches were also dug to make assault on the walls difficult. The main purpose of the castle at this time was to maintain control of the area after the harrying of the North.
Its remains are particularly well-preserved because it is one of only a few castles which were largely unaffected by the Wars of the Roses and the Civil War of the 17th century.