Helmsley is a market town and civil parish in North Yorkshire, England. Historically part of the North Riding of Yorkshire, the town is located at the point where Ryedale leaves the moorland and joins the flat Vale of Pickering. Helmsley is situated on the River Rye on the A170 road, 14 miles east of Thirsk, 13 miles west of Pickering and some 24 miles due north of York.