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.

Ryedale was a non-metropolitan district in North Yorkshire, England. It was in the Vale of Pickering, a low-lying flat area of land drained by the River Derwent. The Vale's landscape is rural with scattered villages and towns. It has been inhabited continuously from the Mesolithic period. The economy was largely agricultural with light industry and tourism playing an increasing role.