The only market town in the 554 square miles of the North York Moors National Park, Helmsley is full of history, character and stunning architecture (including 51 listed buildings) making it a great place to visit. Helmsley is where the North York Moors National Park meets the Howardian Hills. It’s where the Cleveland Way meets the Ebor Way and the Inn Way. It’s where the valleys of Bilsdale and Ryedale leave the moorland and meet the flat Vale of Pickering.