Cleveland Way
From OpenStreetMap Wiki
The Cleveland Way runs from Helmsley around the edge of the North York Moors National Park to Guisborough, then out to the coast and down that as far as Filey.
The waymarks used are a white acorn on a black background.
Progress
The paths from Kildale to Roseberry Topping (and into Guisborough woods) appears to have been mapped.
Relation ID 31112 (work in progress).
Links
Cleveland Way in Wikipedia and at LDWA [1]