Helmsley is a market town and civil parish in the Ryedale district of North Yorkshire, England. The town is located at the point where the valleys of Bilsdale and Ryedale leave the higher moorland and join the flat Vale of Pickering. It is situated on the River Rye and lies on the A170 road, 14 miles east of Thirsk, 13 miles west of Pickering and some 24 miles due north of York.
The Cleveland Way National Trail starts at Helmsley,
It is an historic town of considerable architectural character whose centre has been designated as a Conservation Area. The town is associated with the Earls of Feversham whose ancestral home Duncombe Park was built overlooking the castle.