The Cleveland Way ~ June 2025

Week 1 - Osmotherley

We met up with our ICA friends in Osmotherley, to walk The Cleveland Way. We planned to be in Osmotherley for the first week, being a central base for our walks on the North Yorkshire Moors. Naturally, we all met up and had a 'Welcome' meal in one of the local pubs, which was very enjoyable. It's a great way to get catch up with everyone and also, to meet a new couple who joinned our group recently. We are a small group of just 5 motorhomes, making 10 walkers in total, which was a very managable number.

So here we are, on our first day, with the minibus taking us to Helmsley, a pretty little village, for the start of our 109 mile walk. Initially across the Yorkshire Moors and then along the coast to finish in Filey. The walk was quite a gentle introduction to the Cleveland Way, crossing through wooded areas, over streams and then a gentle climb up to fields to Sutton Bank, where, hurrah, our minibus driver, John, who we later named Whisky John, was there to meet us and take us back to Osmotherley. 


So day 2 we picked up the trail at Sutton Bank, where we left off yesterday. Walking today along the steep sloping western edge of the North Yorkshire Moors, with far reaching views across the plains, with the final stretch into Osmotherly walking on open moorland, which sadly was lacking in heather, but the final sting in the tail, was a killer decline and then a sharp uphill before finally descending into Osmotherly. Thankfully, one of the pubs was open, so we all decided to indulge in some refreshment, before the final hill to our campsite.



Wednesday was a rest day, so I took the opportunity of meeting up with a school friend from Junior school, who just so happened to live up this way in Stokesley. It was so good to meet Clare after, well it must be 50+ years and amazing that we've only just got back in touch with each other. We had a lovely day together and amazingly, we were able to just hit it off straight away. Thank you Clare and Alan for a lovely day and your kind hospitality. Clare and Alan do a lot of walking and are looking to possibly buy a motorhome, so potentially new recruits for the ICA 😊


Thursday was the hardest day of the week. It wasn't such a long walk, but it was hard going. It is described in the book at being remarkably hilly, like a monstrous roller coaster. It was quite stunning in parts, but, we had managed to miss the bad weather that we could see in the distance. We stopped towards the end for a break at a cafe and relaxed for a short while only having 3 miles to go. But that 3 miles was a killer. It was a constant up and down, ending up having to scramble through the Wain Stones. At one point it was so narrow between the rocks that it was hard to pass through with a rucksack on. However, after that it was a steep descent to our waiting minibus. We ended up being 2 hours late that day. That last 3 miles took forever. Thank goodness Whisky John was able to stay and wait for us at Claybank.



Friday, we picked up the trail, which is the remotest part walking along high and exposed moorlands and traversing the highest part of the North Yorkshire Moors to end up at Kildale. Today, we did have a light shower when we first headed off, but if I recall, that soon eased. It seemed that no sooner had you put your waterproofs on, then they needed to come off. We have so far been so lucky with the weather.








Saturday, started off with a big uphill climb but once we got to the top, we were at Captain Cooks monument. The views from here were fabulous, we could see Roseberry Topping from here, and since we didn't have time to detour and climb that, we were pleased that this climb afforded the same views. Our walk took us through wooded areas, still plenty of hills to climb but eventually, leaving the moors behind and heading towards the coastal resort of Saltburn by the Sea. We had made quite good progress here, so we stopped for a quick drink before Whiskty John picked us up and took us back to camp. Tomorrow, is thankfully a rest day and a move day. So we said goodbye to Whisky John, not knowing whether we would see him again for our last minibus pick up at Filey.








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