It runs 110 miles between Helmsley and the Brigg at Filey, skirting the North York Moors National Park.
In 1969 the 110-mile Cleveland Way opened, this was the second National Trail in England and Scotland to open. The route is a walk of two halves. Starting in Helmsley on the edge of the North York Moors it crosses farmland, woods, and beautiful heather moorlands then following along the dramatic coastline finishing in the seaside resort of Filey.
Shepherds Walks Holidays offers an 11-day walk along the full Cleveland Way or if prefer a shorter trip why not walk the Moorland Section or the Coastal section on a shorter holiday.
Self guided walking holiday along the Cleveland Way
Self guided walking holiday along the stunning Heritage Coast
Self guided walking holiday crossing the North Yorks Moors