Cleveland Way Self-guided Holidays

The 110-mile Cleveland Way is a National Trail in ancient Cleveland in northern England, one of the best long-distance trails in the UK. Enjoy one of our self-guided walking holidays along this long-distance trail.

The Cleveland Way runs 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 Trial 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 if you are looking for shorter holiday.