Cleveland Way

The North Yorkshire Moors National Park sits between York and Newcastle in North East England, is bordered by the North Sea to the east and covers an area of some 550 square miles. Skirting around roughly two thirds of its border, the Cleveland Way is the second oldest national trail in the U.K. and highlights the very best that the region has to offer. From twelfth century monastic abbeys, over heather moorland, via rugged sea cliffs to secretive smuggling villages, the Cleveland Way packs an awful lot into a very small space.     

The trail begins in the south west corner of the park at the market square in the lovely village of Helmsley. Initially heading directly away from the final destination may seem disheartening, but this is a trail to be savoured rather than rushed, and wandering through lanes, fields, woodland and gentle river valleys sets the tone for the first section of the walk. An early diversion to the Cistercian Rievaulx Abbey is a must for all, history fan or no, and you should soon take another diversion for the fantastic views and the White Horse hill painting at Roulston Scar.

The views west continue through the high moorland of the Hambleton Hills before the trail drops down into the pretty village of Osmotherley with its village green featuring a stone barter table. A series of small hills then leads into a long section of moorland over Urra Moor, the high point of the trail at 454m, and the distinctive hill at Roseberry Topping. Skirting the town of Guisborough, brings us to the halfway point of the trail as we reach the coast at the Victorian resort town of Saltburn.

The remaining portion of the trail is markedly different in character from the previous moorland sections. The trail now follows the coast over cliffs and dunes and through picture postcard fishing villages like Staithes where the smuggling used to bring in far more revenue than the fishing yet places like the derelict Port Mulgrave are testimony to the modern decline of the fishing and smuggling industries. After a good few more miles of marvellous cliff top walking, Whitby is the next large town.   

It has charm and history aplenty; associations with Dracula and Captain Cook, an abbey on the hill opposite the town, a history of whaling and fantastic fish and chips. Whitby is definitely worth some exploration time. Then it's on, over mile after mile of wonderful sea cliffs through the most famous smuggling village of them all, Robin Hood's Bay, before we reach the two seaside resort towns of Scarborough and Filey. Scarborough and Filey are both creations of the Victorian era with grand sea-front hotel facades and bandstands being the defining characteristics of both towns. Scarborough is by far the bigger and grander of the two but they each have their charm, with Filey's claim to fame, for our purposes at least, being the end of the fantastically varied and interesting Cleveland Way.