Cleveland Way National Trail

Start: Helmsley
Grid Ref: SE 614939
End: Filey
Grid Ref: TA 119809
Distance: 176 km
Walking Time: 9 days
Counties Traversed: Yorkshire
Explorer™ Maps: OL26, OL27

The Cleveland Way route follows the perimeter of the Yorkshire Moors National Park in a large horseshoe loop. There are two distinct sections. The first half heads north through the Hambleton Hills and then east across the heather clad Cleveland Hills to the coast at Saltburn. The second half is a spectacular Heritage Coast walk southwards to Filey.

Helmsley is a small market town overlooked by it's imposing castle ruin. It is from The Cross in the Market Square here that he first westward section of the route begins, passing through the quiet paths and woodland of Ryedale valley. One of the highlights of this section is Rievaulx Abbey, its isolated ruin a haven of serenity. The route generally rises and at Sutton Bank there are splendid views of the Vale of York to the south. The route then turns north to follow the edge of the North York Moors National Park along the Hambleton Hills ridge. The panorama to the west remains as the route, in part following an old drover’s road, continues to Osmotherley. From here the more dramatic scenery of the bracken and heather clad Cleveland Hills begins.

The direction changes to north east as Whorlton Moor, Cringle Moor, Carlton Moor and Urra Moor are traversed. Hasty Bank on Urra Moor provides perhaps the best viewpoint on the whole route. Urra Moor is the highest point on the route at 454m (1489ft). The route from here to the village of Kildale is wild and open moor, best seen in late summer when the purple heather spectacularly clothes the moor. Shortly after Kildale Captain Cook's Obelisk is passed and it is worth making the short detour to the unusual profile of Roseberry Topping, a conical hill with layered slopes. From here to the coast there are extensive remains of the alum workings which were the birth of Middlesbrough's economic growth.

The coastal route south follows the cliffs closely, so reasonable care is required as the friable rocks are liable to subsidence in places. This is an invigorating coastal walk on high cliffs, reaching 220m at Boulby, the highest in England. Several interesting villages are passed on the route including Staithes, but the highlights of this section are Whitby Abbey and Robin Hoods Bay.

Parts of this route traverse wild open moorland and it is recommended that it is not attempted in winter months unless you are a member of an experienced party. The weather can change quickly with fog from the North Sea creating quite sudden loss of visibility. However, providing you are properly equipped and are fit, this trail will provide a memorable experience of remote open spaces and stunning coastal scenery.

An nine day itinerary is recommended to walk the Cleveland Way

Helmsley - Sutton Bank 10.5m
Sutton Bank - Osmotherley 11.5m
Osmotherley - Clay Bank 11m
Clay Bank - Kildale 9.5m
Kildale - Saltburn-by-Sea 15m
Saltburn-by-Sea - Sandsend 17m
Sandsend - Robin Hood’s Bay 10m
Robin Hood’s Bay - Scarborough 14m
Scarborough - Filey 11m

The Tabular Hills Link is an additional route linking Scalby Mills to Helmsley and thus making the Cleveland Way a circular route, useful if you want to start and finish at Helmsley for transport reasons. To do this either retrace your steps from Filey to Scalby Mills or divert onto the Tabular Hills Link at Scalby Mills, and so miss the Scarborough to Filey stage of the Cleveland Way.

The Tabular Hills Link can be done as a three day itinerary as below, but involves three demanding days walking.
Scalby Mills to Levisham - 21 miles
Levisham to Hutton-le-Hole - 15.5 miles
Hutton-le-Hole to Helmsley - 13.5 miles.

We have a selection of walking guidebooks for the Cleveland Way. Click the book image above for details or purchase.