The Shepherd’s Round: The Wainstones to Fangdale Beck

Walking on the Shepherd's Round in the North York Moors.

Despite our best intentions at the start of the summer, our progress with the Shepherd’s Round over in the North York Moors has been slow. The next leg for us to complete was the longest stretch we’d need to tackle, and with spotty weather at the weekends throughout August (and when it was good, I was out making the most of the sunshine with my horse), I blinked and suddenly it’s been two months since our last excursion on the trail.

With the longer days of summer dwindling at an alarming rate and a 12 mile section awaiting us, we bit the bullet during the first weekend of September and got back out on the walk. Having finished our last walk at the Wainstones, from here it was either a 7 mile walk to Cockayne or a 12 mile walk to Fangdale Beck. While 7 miles was more appealing to me, Cockayne is extremely remote and would’ve taken over an hour to drive to in order to drop the second car off, whereas Fangdale Beck was only a 15 minute drive from our starting point. Linear walk logistics ruled the day and the longer route it was.

Walking on the Shepherd's Round in the North York Moors.

Parking is free in a large lay-by at the roadside near the Wainstones, and then we headed straight up the hill on the opposite side of the road to follow the Cleveland Way (and the Coast to Coast) up Round Hill. The climb is steeper nearer the bottom and eases off as you approach the summit, where there’s a trig. Having checked the weather forecast and seeing we were due rain just after lunch time, we didn’t hang around here, powering on at a fast (for me) march to try and beat the rain.

The next few miles were nice and flat, using good moorland tracks, and before I knew it we were 6 miles in after around 2 hours – certainly approaching a personal best pace for me! The views aren’t massively inspiring (although looking back perhaps this is a bit harsh), being surrounded by moorland and not much else in terms of features of interest, although if we’d been here a few weeks earlier I’m sure the heather would’ve been putting on an excellent show.

Walking on the Shepherd's Round in the North York Moors.

Soon we left the Cleveland Way, which peeled off to head towards Kildale, and not long after we left the Coast to Coast too. This next stretch had some of the best views of the walk, although it was unfortunately also the end of the lovely moorland tracks, which slowed my pace a little. We dropped down into the very remote hamlet of Cockayne, where we saw plenty of sheep and not much else, stopping for lunch at the side of the road to re-fuel before the climb back up the hill.

It’s a steep climb up the road to leave Cockayne, but over quickly enough to make it not too bad. Here is where our successful route finding ended, with us sticking to the footpath as shown on the OS map rather than the ‘obvious’ path walked into the moor. A mile or so (probably less but it felt like more) of tramping through heather (thankfully dry) eventually saw us successfully pick up a very faint trail running across the moor – look out for small cairns occasionally marking the path.

Walking on the Shepherd's Round in the North York Moors.

Anyone else who dislikes traipsing across pathless terrain as much as I do will appreciate the pure joy I felt when we eventually picked up a good track for the mile or so of remaining moorland walking. We spotted way markers for St Aelred’s Way, a 41 mile pilgrim trail linking a number of churches in this part of the world with Rievaulx Abbey, and followed it briefly to drop down off the moor.

Here ended our lucky streak of not coming across many cows on the Shepherd’s Round. Our descent took us through several fields with plenty of ‘evidence’ of cows (thankfully empty), and we had a few false alarms where it looked like there were cows in the field only to spot fences between us and them as we got nearer, but in the final field our luck ran out.

Walking on the Shepherd's Round in the North York Moors.

What appeared to be a herd of cows watching us from the next field, actually turned out to be a herd of cows in the same field which just looked like a different field from further away. Worse, we had to walk right past them to get onto the track leading back to the car: and the gate onto said track was propped open. Being followers of the countryside code, we know that you should always leave gates as you find them, although on this occasion it was extremely tempting to slam it shut behind us. Especially as they were stamping their feet at us and a few started walking towards us!

Leaving the gate open, we legged it down the track as fast as we could without actually running, and thankfully the cows didn’t pursue us. I’ve never been more relieved to see a gate out of a field! Feet aching but glad a) to have beaten the rain and b) to have escaped the cows unscathed, it feels like a big section ticked off – leaving just 15 miles to go.

Walking on the Shepherd's Round in the North York Moors.

Dog friendly rating: 3.5/5. This walk gets bonus points for being stile free and for being nice and quiet once you leave the Cleveland Way. It loses points for having sheep throughout, the chance of coming across cows in a few places, and the number of birds (which, if you have a dog like Merry, means leads on at all times). There’s a section of road walking in the middle but this is pretty quiet and we heard most cars long before we saw them. There is very little in the way of accessible water for dogs, so you’ll need to carry extra for them.

Dog walking in the North York Moors on the Shepherd's Round

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