Cleveland Way Walking Holidays

The Cleveland Way offers remarkable variety, from the peaceful uplands of the North York Moors to the ever-changing skies and craggy coastline of Yorkshire. Beginning in the market town of Helmsley, the first half of the trail meanders through woodland, ancient abbeys and wide moorland ridges. The second half opens out onto the coast, where you follow clifftop paths above the North Sea, passing fishing villages, hidden bays and wide beaches. This is a route for walkers who appreciate contrast—quiet, expansive moors one day and the buzz of seaside towns the next. It’s a journey shaped by heritage and landscape, with plenty of rewarding overnight stops along the way.

What makes the Cleveland Way particularly striking is its dramatic contrast — no other National Trail in England transitions so seamlessly from heather moorland to rugged coastal cliffs. You begin immersed in the sweeping solitude of the North York Moors, where curlews call across the open hills and ancient stone crosses mark the way. Then, without warning, the trail tips you onto the edge of the sea, revealing some of Yorkshire’s most iconic coastal views. There’s an extraordinary sense of history underfoot too: from the haunting ruins of Rievaulx and Whitby Abbey to the storied smugglers’ coves that line the coast. Literary connections run deep here, with Bram Stoker drawing on Whitby’s gothic atmosphere to inspire Dracula. This route offers not just scenic grandeur, but a walk through centuries of culture, folklore and resilience. Whether you’re drawn by the wilderness or the waves, the Cleveland Way captures the spirit of northern England in all its rugged beauty.