Cleveland Way

Cleveland Way is a National Trail in the historic Cleveland area of North Yorkshire, England. It’s a multi-day hiking route that runs from Helmsley to the coast at Filey, combining North York Moors inland moorland walking with sections along the North Sea coastline.

The trail is waymarked in both directions using the standard National Trail acorn symbol, so you can plan either north/eastbound or south/westbound itineraries—most walkers still start at Helmsley and finish at Filey.

A practical way to think about the route is as two broad halves: an inland section through the North York Moors and a coastal section that continues to Filey. The inland miles include classic landmarks such as Rievaulx Abbey and the Kilburn White Horse area, then carry you across higher moor tops with Urra Moor (the route’s highest point) and Roseberry Topping in the mix.

After the inland section reaches the coast around Saltburn, the walking increasingly follows the tops of sea cliffs and passes through seaside settlements including Skinningrove, Staithes, Runswick Bay and Sandsend before reaching Whitby. From Whitby the route continues along the cliff tops through Robin Hood’s Bay and Ravenscar, then picks up the coastal approach into Scarborough and continues to Filey near Filey Brigg.

Within the North York Moors National Park for most of its length, Cleveland Way also links with other long-distance trails: the coastal portion aligns with the England Coast Path and the North Sea Trail; the inland stretch between Osmotherley and Bloworth Crossing also intersects the Coast to Coast Walk at Robin Hood’s Bay.

The route was officially opened in 1969 and is guided throughout by the long-distance trail framework used for National Trails (waymarking, sustained maintenance and published route information). Expect a long day count—typical completions are around 7–9 days—so break the route into manageable sections with time for the major towns and coastal crossings at key points.

For planning, use the established access points along the line: Helmsley for the start, then widely-used drop-in areas such as Rievaulx Abbey, Sutton Bank, Osmotherley, Carlton Bank, Kildale, Slapewath, Saltburn, and the coastal towns up to Filey. This makes it straightforward to hike the full route, or to build a linear multi-day section using the same waymarking and connections.

More information: Wikipedia, Cleveland Way, Watch: Walking the Cleveland Way in England