The Cleveland Way is one of Britain's better long distance paths. It is a trail of two halves; it starts off from the mooorland village of Helmsley, then heads west to the escarpment of Sutton Bank. It then heads north along the escarpment and across moorland before descending down to reach Osmotherley.
The hardest and remotest stretch of trail then follows as the path heads east, climbing up and down a series of hills before eventually passing the highest point of the moors, after which it slowly descends northwards to Kildale. It then climbs north, passing the Captain Cook Memorial to reach an official diversion that visits the outlying summit of Roseberry Topping. The trail then heads northeastwards, heading through Guisborough Woods and visiting the villages of Skelton Green and Skelton before reaching the North Sea coast at Saltbun-by-the-Sea.
Whereas the first half of the trail crosses wild and remote moorland, the second half is a sometimes-high and wild coastal walk. A clifftop walk leads to the village of Skinningrove, after which a visit to the highest cliffs on the east coast of England leads to Staithes. More clifftop walking leads to Runswick Bay, Sandsend and then the town of Whitby.
An easier walk heads along cliffs to Robin Hood's Bay, after which a high climb leads up to the incomplete village of Ravenscar. The trail then sticks to the clifftop as it heads south to visit Scarborough. The trail follows the promenade through the town before climbing up the cliffs to the south. An easy and rewarding stroll along the cliffs then leads to the end of the trail at Filey Brigg.
The varied nature of the trail makes it a wonderful stroll, with the high views and wild scenery of the moors contrasting sharply with the rugged coastal stretch of the trail.
Map of the trail
Maps courtesy of Google Maps. Route for indicative purposes only, and may have been plotted after the walk. Please send me have comments you may have on what you think of this new format.
The western part of the trail is not well-served by public transport; most of the villages (aside from Helmsley and Ostmotherley) sit off the trail on the plains below.
The coastal stretch is much better served, and various bus services run up and down the coast; there are also railway stations that allows the coastal stretch between Saltburn and Filey to be walked in one go.
There are railway stations on or near the trail at Kildale, Saltburn, Whitby, Scarborough and Filey.
Traveline is a very good resource for planning journeys by public transport.
Landranger 94 (Whitby & Esk Dale, Robin Hood's Bay)
Landranger 101 (Scarborough, Bridlington & Filey)
The following schedules are advisory. They indicate various ways that the trail can be split up into walks of several lengths, with convenient end-points for each day's walk.
Naturally, you may want to alter this according to whether you are staying in B&B's, hostels, camping or are doing the walk in sections and are relying on public transport. Your own walk will probably vary from the itineraries shown below.
Robin Hoods Bay
Robin Hoods Bay
The inland half of the Cleveland Way can be difficult to split up into short legs without diverting off the trail onto the plains. Accommodation, especially between Osmotherley and Kildale, is sparse. The coastal stretch is very different, with regular villages on the coast and others a short distance inland, and some fairly good transport links.
Note that any leg ending at Carlton Bank involves a walk to the nearest accommodation; usually this would be a walk of 1.5 miles down into Carlton-in-Cleveland, or even further into Swainby. Care needs to be taken when planning the stretch between Osmotherley and Kildale.
There are several tourist information offices on or near the Cleveland Way. These are not necessarily open throughout the year; see the websites for opening times. Also note that these have been closing in recent years, which means that this list may not be fully accurate - if you spot any problems, please let me know.
The Cleveland Way can be walked at any time of year; however, you would be wise to avoid walking it in the winter without a great deal of walking experience. The high moors inland can become snowbound for weeks at a time, and the coastal paths can be very slippery. Worse, some useful accommodation closes during the winter.
The best time for walking the trail would between April and September, outside the school's summer holidays. Accommodation should be plentiful through this period, and there is plenty of daylight in which to complete the longer stretches.
In late summer / early autumn, heather on the moorland stretches can provide a vivid display of colour.