Day-by-day trail itinerary

Cleveland Way: 9-day itinerary

Three quite different kinds of walking before the moors proper. Out of Helmsley it is Rye valley farmland and steep-sided broadleaf woodland, with stepped paths through the trees that go greasy after rain, past Rievaulx and up Nettle Dale on firm farm tracks. At Sutton Bank the ground tips over onto the limestone escarpment and stays on the lip of it, soft grass along the top of a long drop with the Vale of York laid out to the west. Beyond Sneck Yate the trail joins the Hambleton Drove Road, a broad old droving track that gives the fastest and easiest miles on the whole route, until the descent off Black Hambleton runs onto a loose, rock-strewn track that is genuinely unpleasant underfoot, and the drop into Oakdale adds lichened stone steps that are slick when damp. Osmotherley is the last village with a full range of services before the escarpment. After it the character changes again onto Scarth Wood Moor, the first open heather of the trail, then down through woodland into Scugdale.