Set on a rocky outcrop overlooking the River Rye, Helmsley castle although in ruins is still impressive with the remains of the east tower still dominating the towns skyline.
Its most impressive feature are the large earthworks with two deep ditches cut down through the rock outcrop. This ringwork formed part of the original earth and timber castle built in 1120 by Walter Espec to watch over his Yorkshire estates. Following his death in 1154 the castle passed to his brother Peter de Roos , and it was to be held by descendants of the de Roos until 1688.
Robert de Roos rebuilt the castle in stone around 1186 and modernisation continued into the 16th century, when the medieval buildings were converted into a fine Tudor mansion , the remains of which can still be seen.
The conflict of the English Civil War resulted in destruction of significant parts of the castle, but it continued in use as a residence until the early part of the 18th century. The current appearance of the castle owes much to Sir Charles Peer’s restoration , after the site passed into state guardianship in 1923.