The Cleveland Way

A Walker’s Journal by Anthony Linick

The Cleveland Way is truly a walk of two halves ¬– but stone walls can be found in many locales throughout the venture.

The Cleveland Way is truly a walk of two halves ¬– but stone walls can be found in many locales throughout the venture.


North Yorkshire’s Cleveland Way, officially inaugurated in 1969, is the second oldest National Trail. I learned of its existence almost by accident – for on the shelves of the library of the American School in London, where I began work in 1982, I found a copy of the trail guide in the old HMSO imprint – and for many years I had hoped for an opportunity to undertake its challenges. This did not occur until 2018 when I did the first half with Gavan, one of my former students at ASL. We did the second half in 2019.

Indeed, the Cleveland Way is a walk of two halves. The first half, from Helmsley to Saltburn, makes its way through uplands and moorland as it circles in a northerly direction to arrive at the North Sea at Saltburn. The second half is a coastal route – which heads in a southerly direction along clifftops to end in Filey. The total distance is some 109 miles – which is why we decided to break the adventure into two parts. Though well within the capabilities of experienced walkers, both halves present challenges – hill summits in the first half, deeply indented stream crossings in the second. We found that the coastal portion presented some special problems after rain had turned the surfaces into a muddy paste ­– and it is worth mentioning that there is a far more congenial alternative in the Cinder Track, which parallels the Cleveland Way from Whitby to Scarborough.

We used three OS Explorer maps in our quest – OL 26 (North York Moors Western Area), OL 27 (North York Moors Eastern Area) and 301 (Scarborough, Bridlington & Flamborough Head). These days purchase of such maps also allows the user to download the maps onto one’s telephone – which is what Gavan did. We also used the Official National Trail Guide by Ian Sampson. This volume also contains narrow sections of the route derived from the OS maps.

There are a number of companies that offer professional assistance in booking accommodation and transferring heavy luggage from place to place. Just type in The Cleveland Way and your search engine will take you to these immediately. In our case Gavan wanted to do all the booking himself. He did a good job of this but there remained the problem of luggage transfer. For this he enlisted the services of the Sherpa Van Company – which covers the entire route. If you are entirely new to the walking enterprise and need some help in getting started you may want to have a look at my A Walker’s Alphabet: Adventures on the long-distance footpaths of Great Britain. This can be obtained directly from the publisher at or or from or

As the accounts that follow will demonstrate we had a terrific time on the route. There were some mishaps but it is easy for me to recommend the Cleveland Way to others. The stages that follow were the ones we used – with mileage figures representing our best guess at the actual distance we covered on each day. A look at this itinerary will create some head-scratching. We seem to have walked the first part backwards, we had to go off-route for accommodation on some days and there seems to be a missing gap. All will be revealed.

Day 1: Rievaulx Abbey to Helmsley – 3.5 miles

Day 2: Rievaulx Bridge to High Paradise Farm – 9.5 miles

Day 3: High Paradise Farm to Osmotherly – 8 miles

Day 4: Osmotherly to Carlton Bank – 7 miles

Day 5: Clay Bank to Kildale – 9 miles

Day 6: Kildale to Newton-Under-Roseberry – 6.5 miles

Day 7: Newton-Under-Roseberry to Saltburn – 12 miles

Day 8: Saltburn to Staithes – 9.5 miles

Day 9: Staithes to Whitby – 12.5 miles

Day 10: Whitby to Robin Hood’s Bay – 7.5 miles

Day 11: Robin Hood’s Bay to Hayburn Wyke – 9 miles

Day 12: Hayburn Wyke to Scarborough – 9 miles

Day 13: Scarborough to Filey – 9.5 miles