After the near misses, and nearly finishes of the South Downs Way, and the Hadrians Wall Path, I am pleased to say I managed to finish another trail!
I can now chalk up The Cleveland Way, next to the Pennine Bridleway, and the Yorkshire Wolds Way, as trails I have officially done. No storms, floods or global pandemics (that was to come later in the year…) interfered with my progress this time out!
And The Cleveland Way, March 1st to March 7th 2020 will live in my memory as some of the best walking I have ever done. Simply fantastic. I got lucky with the weather, the trail was quiet, my fitness was improving and the views were quite simply fantastic.

This was probably my 2nd favourite distance trail so far, only pipped from top spot by the non-national-trail (although surely it should be…) Wainwright’s Coast to Coast walk, which I must try to do again. There is something about not faffing with public transport, and being able to stop and start your walk on the trail that I like. No half hour bus rides to a reasonably priced hotel, no re-planning around poor weather. Eat Sleep Walk Repeat. Simple.
My dad dropped me off in Helmsley on Sunday May 1st and I set off in the direction of the White Horse. Truth be told, if the official route didn’t divert alongside the gliding club at Sutton Bank then I wouldn’t have bothered trekking out to the Horse and back. It seems odd to me to get such a close up view of something you can only see properly from the sky / a long way away!
That said – the view on the way to the Horse is stunning, and that is the reason to follow the trail out and back whilst looking out for low swooping hang-gliders. One of the finest views in England. Follow that link for an example – my poor photo on an iPhone 8 with a cracked camera, didn’t do it justice. But it was spectacular.

Still – my rule for the trails is to follow the signs on the ground – for fear of missing a bit and not being able to claim I’ve bagged the whole trail. I’m glad I did because the vista is worth it.
I stopped the first night at High Paradise farm, which is idicliic. These friendly dogs met me whilst I tucked into a delicious beef stew, which was an upgrade on the self catering option I’d planned. Day 1 an easy 24km.

Day 2 and 3 I walked about 30km each, and it took me to Great Broughton, and then on to Newton under Roseberry top.
Day 4 started with the climb up Roseberry topping for a panoramic view back along the trail, and then onwards to the sea side. 18km.

Day 5 took me down the coast to Whitby. About 35 km. Stunning. I’d let the pics do the talking if I had taken any good ones… Wonderful walking, go and do it.
Day 6 was only really a half day, and I arrived in Robins Hoods Bay with perfect timing after just 12km from Whitby for a couple of pints whilst the tide went back out. I went to the same pub I visited at the end of the Coast to Coast walk. After that I strolled along the sand to the YHA, and snuck around the corner in between waves to make it to Boggle Hole. Boots needed a wash anyway!
Day 7 was a long one. I had in mind the idea of not stopping in Scarborough when I planned the trail, and doing a long final day, rather than an eighth day. My thinking was that a 40km day would do me good, get me home a day early, and save me £40 in Travelodge costs. So at 5 to midday, I cancelled my hotel and decided it was Filey Brigg or bust. Cleveland Way done. And plenty of calories earned for the rather large takeaway I ordered on the way home!

Anyroad – here are the day charts…
Day 1 – Helmsley to High Paradise

Day 2 – High Paradise to Great Broughton

Day 3 – Great Broughton to Newton Under Roseberry

Day 4 – Newton Under Roseberry to Saltburn by the Sea

Day 5 – Saltburn by the Sea to Whitby

Day 6 – Whitby to Boggle Hole

Day 7 – Boggle Hole to Filey Brigg and Finish.

And a gallery of pics from along the way… sorry about the quality, I either need to take my SLR or buy a new iPhone before the South West Coast Path!
Cap’n Cook Whitby Abbey, not finished. The finish!