In my direction, there’s a nice little prologue between Filey and Scarborough, which I took as a one-off before returning a few months later for the rest of the cliffs all the way to Saltburn. (Because I started from Filey station and followed the Wolds Way to the Brigg, this will also help when I come back to finish that National Trail.) One of my favourite seaside towns, Whitby, was well placed for a couple of overnights, and there are other very touristy spots including Robin Hood’s Bay and Sleights.
After another short break, I was back at Saltburn for the climb up onto the moors. For the most part, the Way sticks to their northern and western escarpments, which provides great long-distance views; almost, then, cliff-edge walking in a different sense. There are no towns and few villages, the most important being Osmotherley, but there will almost certainly be other walkers around at Roseberry Topping (or ‘the iconic Roseberry Topping’ as it now seems to be officially known) and Sutton Bank. The finish town of Helmsley is one of those perfect little Yorkshire market towns.
There are rail services to Filey, Scarborough, Whitby, Saltburn and Kildale – the latter is the only rail access within the moorland section. Filey is on a none-too-frequent branch line from Hull to Scarborough, and both Whitby and Kildale are served by the four-trains-a-day Esk Valley line to Middlesbrough, so neither of those lines is fantastically useful for visitors from far afield. Scarborough and Saltburn though have direct links to the major rail hubs of York and Darlington respectively.
There are good bus services from Scarborough to Whitby, and Whitby to Middlesbrough, that run not far from the coast and venture on to it at places like Robin Hood’s Bay. The former was invaluable to me in planning – it meant I could have a couple of nights in Whitby and walk with a day pack in between. There are almost no bus services on the moors, apart from those serving Osmotherley and Sutton Bank, and you’ll need a bus to get back from Helmsley – there’s a useful service direct to York.
Accommodation (including camp sites) is plentiful along the coast, though it could get heavily booked in the summer. Again, there is less on the moors, and in particular as of 2018 there was nothing in easy reach on the 20 miles from Kildale to Osmotherley. Wild camping, even if it were legal, is of scant help, as there is little in the way of reliable water supply. In essence therefore, the moorland section needs much more careful planning than the coast, unless you are willing to put in 20-mile days or use a pick-up service – there are plenty who do the latter, and many firms to provide the service.
Walking the Cleveland Way
There’s a page for the coastal section and another for the moorland section.