Heather-clad moorland and superb coastal scenery are the dominant feature of this rugged trail, which follows a giant horseshoe around the North York Moors National Park. From its west end at the pleasant market town of Helmsley to the east end of the small seaside resort of Filey.

The views are ever-changing, far across the counties of Yorkshire and Cleveland, or out to the sea. The trail takes its name from the Cleveland Hills which provide the highest points, reaching 1378 feet (420 metres) at Cringle Moor. Here the route follows the ridge which is quite isolated at times, and you must usually divert from the path to reach your overnight accommodation.The coast is reached at Saltburn, then you follow the clifs all the way to Filey, often descending to pass through fishing villages, harbours and resorts of all sizes including Whitby, Scarborough and the quaintly named Robin Hood’s Bay.