During the reign of King Henry III (1216–1272), Pickering Castle saw further development. The political instability of the period, including baronial rebellions and external threats, necessitated stronger fortifications.

Additional Towers and Battlements

New towers were added to the curtain walls, improving surveillance and defensive capabilities. Battlements and walkways allowed defenders to patrol the walls and repel attackers.

The Gatehouse

The gatehouse was reinforced with a portcullis and arrow slits, enhancing the castle’s ability to control entry and defend against sieges.

Pickering Castle and the Wars of the Roses

During the Wars of the Roses (1455–1487), a dynastic struggle between the Houses of Lancaster and York, Pickering Castle played a minor but notable role. The castle changed hands depending on local allegiances, and the town of Pickering suffered from the turmoil of the conflict.

However, Pickering was never the site of a major battle during these wars, unlike other castles in Yorkshire. Its importance was more symbolic and administrative. shutdown123