High moorland ridges and rugged coastline linking upland and sea across northern England
The Cleveland Way forms a wide arc through North Yorkshire, running from Helmsley at the edge of the Howardian Hills National Landscape, across the North York Moors National Park, and along the dramatic coastline to Filey. The route brings together two distinct landscapes, beginning with elevated moorland walking before turning east to follow high cliffs above the North Sea.
Walking here is shaped by contrast. Inland sections cross open heather moorland and long escarpment edges, where steady climbs lead to broad views across valleys and farmland below. The terrain is generally firm but exposed, with gradients that demand sustained effort rather than technical skill. As the route reaches the coast, the character shifts to clifftop paths, headlands, and small fishing settlements spaced along the shore.
The trail feels spacious and often quiet, particularly across the moors where long distances separate villages. Woodland sections and river valleys provide shelter at intervals, while historic sites such as abbey ruins and coastal landmarks punctuate the journey without interrupting its overall flow.
A defining feature of the Cleveland Way is its sense of progression between landscapes. The transition from upland moor to open sea feels gradual and deliberate, reinforcing the feeling of a complete journey rather than a single-type route. Coastal sections often feel more social, while inland stretches return quickly to solitude and open ground.
The appeal of the Cleveland Way lies in its balance. It combines long, steady moorland walking with some of England’s most striking coastal paths, offering variety without losing coherence, and rewarding walkers who enjoy space, distance, and changing terrain.
Trail Overview
Distance
Approximately 109 miles / 175 km
Typical time on foot
7–9 days
Start
Helmsley, North Yorkshire
Finish
Filey, North Yorkshire
Terrain
Moorland paths, escarpment tracks, woodland trails, coastal clifftops, villages, and minor roads
