The Cleveland Way was opened in May 1969; the second of the British National Trails after the Pennine Way. It stretches for approximately 110 miles/177km along the edge of the North York Moors and the North Yorkshire Coast and reaches its highest point on Urra Moor 454m (1,489ft). The scenery encompasses farming landscapes and forests - some have hardly changed for centuries - dramatic rolling country with abrupt scarps and sandstone edges, bleak moors, dramatic cliff and beach seaside scenery. It semicircles the largest open moorland in England and then follows the Heritage Coast on top of rugged, but grassy cliffs. Eighty percent of the trail is within the North York Moors National Park.

All this moor and cliff walking is punctuated at intervals with interesting market towns and sleepy fishing villages, steeped in historical and literary associations. Examples include Helmsley Castle, Rievaulx, Robin Hood's Bay, Whitby Abbey, Staithes Harbour, Captain Cook (who grew up near Roseberry Topping, worked at Staithes, and set sail in 1747 from Whitby Bay), Count Dracula (who dined out on the locals at Whitby), and James Herriot (the vet who got dragged or chased through the fields by intemperate domestic animals!)

Although not as physically dramatic as the Lake District, this area does boast a distinctive, sublime beauty of its own, it also tends to have a more clement, drier climate. The walk must not be underestimated, there is a lot of ascent and descent throughout, traverses over high moorland and some steep inclinations.

Highlights of the Cleveland Way include, the remains of the Norman Rievaulx and Whitby Abbeys, the Captain Cook Monument, Robin Hoods Bay with it's cliff-hanging cottages, Staithes (pronounced Stairs) a famous old fishing village and Scarborough, the quintessential Yorkshire seaside resort.