Helmsley Castle is a massive rectangular earth ringwork and baileys fortress, founded by Walter L’Espec in 1120. In the late 12th and 13th centuries, Robert de Roos and his descendants encased its inner platform with a curtain wall, flanked by gatehouses, round towers at the angles and in the centre of the east curtain wall, a great round-front keep. Double rock-cut ditches and huge counterscarp banks, surround the inner bailey, with outer baileys and 13th century barbican gatehouses, giving defence to the north and south entrances. In the 16th century, the Manners family remodelled the castle’s chamber block into a luxurious mansion but sadly the substantially altered keep, was slighted after the Civil War. 5 miles south is Gilling Castle and 13 miles east is Pickering Castle.