Ruins of Helmsley Castle which comprise a formidable double ditch, hewn from solid rock on the west side, surrounding an oblong inner bailey. The concentric rectangular ringwork is generally attributed to Walter lEspec, founder of the nearby Rievaulx Abbey, who held the site from 1120 to 1153. The massive earthern rampart between the deep ditches was probably originally surmounted by a timber stockade. A stone castle was raised by Robert de Roos some time between 1186 and 1227. The curtain wall enclosing the inner bailey featured circular towers protecting 3 of the 4 corners, 2 semi-circular towers flanking the northern gatehouse plus a larger projecting D-shaped tower keep located on the eastern curtain. On the western side the curtain wall is sharply set back roughly half-way along its length and a square tower situated in the angle. A simple gate tower provided access on the southern side. A range of domestic buildings including a great hall were situated on the west side of the inner bailey. The entrances were strengthened in the mid 13th century with the addition of an outer gatehouse in front of the north gate and a large barbican beyond the south gate. During the 14th century the south barbican was strengthened, 2 upper floors were added to the keep and a new hall built in the south west corner. In the 1560s Edward Manners, 3rd Earl of Rutland, built a house in the shell of the west tower which survives largely unaltered. In November 1644 following a 3 month siege the castle surrended to the Parliamentary commander Sir Thomas Fairfax and its subsequent slighting was severe. Most of the curtain wall and towers survive only as footings although the courtyard front of the keep stands almost extant. Scheduled and in guardianship.