Text Box: This early 13th century castle is surrounded by a formidable double ditch cut from solid rock. The founder of nearby Rievaulx Abbey is believed to have had a castle on this site at the beginning of the 12th century, but the de Roos family developed Helmsley over the next three centuries. Roughly oblong in plan, the inner bailey is enclosed by a curtain wall, now only standing to a low level, and guarded by an arrangement of circular and semi-circular towers. The south barbican provided access to the inner bailey, and was constructed as an outer gatehouse flanked by two cylindrical towers. From inside the barbican the typically 13th century open-backed towers can be best observed. Now largely ruinous, the south gate still shows the slot for the portcullis on the west side. To the north of the inner bailey, only the basement levels of the two gate towers remain, and beyond that the north barbican formed an outer gate, also flanked by cylindrical towers.

Helmsley Castle