The Cleveland Way. Helmsley to Somewhere On The North York Moors

Day 1. 19 miles

It would be a sensible thought that, following a gruelling summer spent planning then walking a Pennine Way, that the next walkathon would be put to bed until at least after the colder months of the year. I’d earned my 2019 stripes over those long days spent traipsing up the spine of northern England. But, it wasn’t long after the completion of the walk that I was back at my desk and began to daydream about the hills, the views, the wondering where I’d wake up and where I’d spend each night. And I realised that putting off another adventure until the new year just wouldn’t do. So, where to go next? Limited annual leave meant that something in the 100 mile mark might just do. The Cleveland Way seemed more than appealing…. It fit the brief. Moors, hills, coastline, space, high places. Autumn. My favourite time of year.

Whereas the Pennine took months of planning due to both its length and the fact that resources and amenities throughout the journey were mostly on the meagre side, and the navigation being more problematic, the Cleveland by comparison didn’t take up too much of my thoughts. Granted, the first half spent up in the North York Moors was more isolated than the coastal section, but I made sure to divide those days into slightly longer sections to ensure that water and food wouldn’t be too much of an issue to obtain, and that the starting point in Helmsley was a perfect place to stock up on provisions just in case I was waylaid during the first fifty miles. Following an overnight stopover in York, I arrived in Helmsley mid-morning and following a lovely breakfast in the Crema Coffee House, I popped into the excellent Hunters Deli for pies and pastries. When I say “popped”, I’d say a more accurate term is dragged inside by invisible forces, after I’d taken a more than tantalising glimpse at all the treats in the window whilst standing in the street outside. My already over-sized bag was weighed down considerably more with the goodies I emerged from the shop with, but like the Pennine, I knew my body and bag would quickly get used to each others presence.

As the Pennine had been so recently completed, comparisons were natural but whereas the first day of the PW is a ballbuster, the Cleveland ensures a gentler start to the walk, and I was eased in through fields and into woodland, admittedly somewhat muddy and occasionally slippy, though going by the time of year, this was hardly unexpected. The terrain was flat and I barely saw a soul during the first half of the day on the ten or eleven miles of unremarkable pathways and scenery to Sutton Bank. That said, the peaceful and sheltered woodland was lovely to walk through. The few drops of rain that I felt not long after starting surprisingly didn’t change into anything heavier going by the darkening of the skies ahead, but as it transpired it wasn’t long until the sun decided to make an appearance as I headed through more fields and then briefly into some civilisation in the pretty village of Cold Kirby, and as quickly as you’re in there it’s back out again to the wet fields and onwards to the A170, which was pleasantly quiet and a doddle to cross.

Another narrow and sheltered path doesn’t give any clues as to what lies at the end of it, which in this case are beautiful views overlooking the Vale of Mowbray that are a constant for the following few miles. These views have been described by James Herriot as “the finest view in England”. As beautiful as the views are, I personally wouldn’t isolate them to that lofty extent but they are up there with some of the best ones I have stood and admired. The patchwork of fields in varying shades of green and varying stages of harvest stretched for miles. There is the option therein to head away from the trail to White Horse. I admit to not feeling enthused enough to do this, especially as I knew there was a cafe at Sutton Bank Visitor Centre and as a pot of tea was more appealing at this point, I retired thusly and took a well earned break for half an hour. I somehow resisted the scones and other baked goods that were tantalisingly on show but with it being day one and my rucksack full of goodies, I restrained myself which most certainly wasn’t easy to do.

The afternoon by contrast to the mornings walking was consistently on high ground and with continuing beautiful views below, though under overcast and chilly skies before the Cleveland emerged into the wide and expansive North York Moors following another spell of dense woodland walking. This was the part of the day I was looking forward to the most, the sheer barren landscape and wilderness of the moors and walking into and across acres of nowhere I found invigorating. I was welcomed to the moors by some warm sunshine which was with me for the rest of the day, and cast beautiful shadows over the heather and the grass as I wearily strolled through and my tired body and equally sleepy mind meant that thoughts began of finding somewhere to spend the night with the days now dramatically shorter than they were three months ago, and wanting to be pitched up in good time for the sunset. The wind had picked up by this point and it was with some luck that I stumbled upon a dip in the ground where I could pitch my tent in relative shelter, though the downside of this was pegging into a rocky floor that meant constantly having to shuffle the tent a few inches in all manner of directions until the pegs were able to penetrate the earth. Eventually, and with no one or nothing around and in a spot in who knows where, I was able to enjoy a packed lunch dinner of egg salad baguette and lemon drizzle cake, a cup of tea and an early night.

Cleveland Way Day Two >