Set in the centre of Helmsley the castle ruins stand proud overlooking this popular and bustling market town. The Castle was built around the 1120's on a rocky outcrop close to the River Rye. Today the ruins still dominate the towns skyline. It was Walter Espec who built the castle within the centre of his estate, Walter was a Norman Noble in the north of England, who enjoyed considerable political success under King Stephen. He held several appointments under his rule and as such amassed great wealth and land holdings in the North of England. 

The castle was built with two bailey's and enclosed by huge earthworks which you can still see today around the site. The castle continued to grow through the Middle Ages with more buildings being built as well as improved defences. This work continued well into the 16th century when it was converted into a magnificent Tudor Mansion, which is still visible today.

It was during the English Civil war that significand parts of the castle were destroyed though it continued as a residence until the early 18th century. Duncombe Park was being built at that time and its estates were formed from many of the castles hunting estates as well as land from the nearby Rievaux Abbey, and the castle eventually became a Gothic ruin within the grounds of the new Duncombe Park.

Today the castle is managed by English Heritage.