Cleveland Way: Day 1

Helmsley to High Paradise Farm (14.5 miles)

Sunday 12th September 2021

At long last and after much delay, I had made it to the edge of the North York Moors and was ready to take on the Cleveland Way! 109 miles to cover, spread across seven-days of walking and with six-nights of camping. Carrying all of my camping gear in the rucksack behind me, along with enough food to see me through the adventure.

Start of the Cleveland Way in Helmsley near York.

It was a long old drive from Weston-super-Mare to get up to this corner of Yorkshire. Well over four hours, including one stop at the services and having left at 5am that morning. I was heading straight for Helmsley and, in spite of one closure along the A170, I made it there… Only to find that I wouldn’t be able to leave my car for a week at the intended spot in the town centre.

Pay and display parking charges apply. Not only that but there are restrictions on what days and hours you can park there in the week. Panic began to set in. After using the public toilets, I drove off towards the signed ‘long stay car park’.

These spaces also came with a pay-and-display requirement but with no option to purchase seven days in advance. Back to the roads I went. Emotion rising. Time pressing on. But I soon found plenty of free and available spaces heading east along the A170 and away from the centre of Helmsley. My car was pointing towards a petrol station that I’d probably use days later when I would come to return home.

For the next few days then, I’d be looking out for a following these white acorns. One benefit of following an established National Trail is that the waymarking is very good.

I’ll be honest; I was in a bit of a state for these first few miles. Partly from the lack of sleep in preparation and then the very long drive up from home. Then there was the minor panic over car parking before I unleashed myself out on to a personally unexplored landscape and National Park with nobody local to call upon for support or assistance if or when required.

On previous walks of The Ridgeway (from Wiltshire) and South Downs Way, I’d always known at least one person who’d be little more than an hour’s drive away at the worst of times.

I passed on the opportunity to take a detour up to Rievaulx Abbey. I’m sure it’s nice but I was reluctant to head off-course so soon in to my journey and I did actually drive past it on the way in, following a diversion from the A-road.

It would be fair to say that I wasn’t enjoying or being fully present in the experience as I might otherwise have been, through this first day on the Cleveland Way. But that’s not to suggest that there wasn’t much to admire and appreciate in the surroundings.

I followed broad tracks through this woodland and very nearly caught up with two walkers ahead of me, who I figured were also walking this trail, on the account of their 40 litre(ish) backpacks. Meanwhile, the 50 litre mass behind my shoulders was bearing a total of 16.5kg… Including one litre of water and enough food for the whole trip.

That other couple turned off in a different direction before I would turn up towards Cold Kirby. Along this next path, I found a suspicious line of dead birds (possibly grouse). I couldn’t think of their cause of death in the moment. But I saw heard a quad bike revving up behind me and figured they’d probably been run over.

I did find a bench in Cold Kirby, stopped to readjust my pack, eat some of my snacks and just rested for a bit. I wasn’t even close to halfway and I was starting to feel it. But I was also moving on past the point of turning back and driving away.

This was the first of two ‘honesty boxes’ that I’d find on this first day. I believe they might be referred to as “trail magic” over in the US. For a small donation, you can help yourself to whatever drinks and snacks the owner has kindly provided.

While I was within the National Park boundary, I was still some way from the North York Moors proper. Whatever was left to come in this day; I knew that I’d be meeting real hills and heathland for the next two days at least.

I then passed another honesty box in the Hambleton area and before crossing the road towards Sutton Bank. But all the flapjacks had been taken and only two small bottles of water remained.

I soon arrived at a path junction along the Cleveland Way. My main route would continue to the north. But, for the sake of it, I decided to take an official linear detail south towards the White Horse figure.

If you can study the photo above, I had to walk out to and just beyond the protruding cliff edge you can see just left of centre.

It was already beginning to feel like a long walk out and only to come back again. But the views away to my right (looking west) were superb.

A well-surfaced path outlined the way forward and it was quite busy, with people of all ages walking along in both directions.

I passed the airfield for the local gliding club on my left. It was pretty busy around here. I’d not seen a gliding club with so much action going on for a Sunday. One of their former members is Amy Johnson, who was the first female to fly solo from London to Australia.

I passed several opportune lunch spots on the way to the white horse. I wasn’t too surprised to find that I was at a vantage point where I couldn’t clearly see it. From the car park below, it’s probably more legible.

At least I can say that I’ve been there – and it counts towards my full completion of the official Cleveland Way route! Apparently this chalk figure (the Kilburn White Horse) was inspired by one man’s visit to Wiltshire and his admiration for the white horses that adorn the downland there.

Back to the northbound route and I soon passed a sign for the “Finest view in England”… I’d heard or read about this in advance but didn’t know quite what to expect. I just found it to be amusing.

Then there was a platform, dedicated to this optimal viewpoint. Thankfully without the queues that you might find on the summit of a mountain like Snowdon. In fact, there was no-one else around for at least five minutes, while I tried to take it in.

To be quite honest. While it was a very fine view, I’d seen many others that morning – particularly around the white horse – that I’d argue could rival it.

From Sutton Bank, I continued, mostly unaware of the nearby National Park visitor centre. Perhaps I’ll visit on another year.

It was around here that I noticed separate routes had been created to keep the walkers from the cyclists and vice versa. I was really impressed with this and had heard, in advance of my own trip, that there’s a long term aim to create a cycle friendly and independent option to the current Cleveland Way. But if you are in to mountain biking then, the North York Moors has so many other bridleways that can be followed and explored.

It was on this long straight and nearing the end of my first day, that I felt the emotions of the morning beginning to resurface. I think it was from being in a space away from people, for the first time properly since walking to and from the white horse.

As I entered the forest of Boltby, there was a sign for High Paradise Farm, where I’d be spending the night in my tent. I really liked the fact that it is not accessible by car (unless you’ve booked a room). For the café and camping, you must only arrive by bike, on horse or on foot.

If you are intending to camp one night, they do ask on their website that you text them on the day of arrival, so that they know to look out for you.

I found a group of people sitting and chatting inside the café at High Paradise Farm, probably ten minutes after closing. It turned out that I would be the only person camping there on this night – the site to myself and all for the cost of £11!

It was breezy and overcast but one of the owners was very happy to take the time to show me around, where I could pitch and even helped to carry a picnic table over, just for me – let me tell you, they are very desirable when you’re backpacking and not carrying any campsite furniture with you!

I do think I’d have struggled here, if I had arrived at a busy site or with other people wanting to chat. That’s just how I am sometimes and, mentally, this had been quite a tough day for me. But I was on the Cleveland Way. Finally! As the hours passed, I began to settle in to the idea that I could wake up the next morning and walk again to my next tent-stop.

I was pleased with the minimalist campsite itself – although it wasn’t until I left the next morning, that I realised there’s a light switch for the toilets and sinks on this side of the wall!! My headtorch had served me well. Being right beside the Cleveland Way (I was standing on the trail when I took the photo above), I would highly recommend staying here and the café is probably worth a look (if you can arrive in time).

Within the 16.5kg load of my rucksack, I was carrying a last-minute gift from an incredibly thoughtful and caring friend. She’d spent her entire Saturday evening hand-writing me six letters – one for each evening in my tent. They were wrapped, sealed with a wax stamp and then delivered to my at around 22:30.

It’s hard for me to put in to words, just how much this would mean to me. I was never going to feel ‘lonely’ on this trek. While I may be walking it alone, she was always beside me in spirit and in heart. I now had these letters to look forward to each evening and I did write replies, if even the next morning. It was almost like continuing one of our regular conversations.

Next time, I’ll write about Day 2 as I continue my journey along the Cleveland Way.

Length of this walk = 14.5 miles

Thanks for reading.

Author: Olly Parry-Jones

I live in Weston-super-Mare, close to the Mendip Hills in Somerset and I enjoy time spent outdoors, whether that's walking, camping or backpacking. My day job involved making furniture from recycled wood (I'm a furniture maker and carpenter by trade). I have two blogs: Olly Writes (woodworking, DIY, baking) Walks With Olly (walking, camping and kit) You can also find me on YouTube, Twitter and Facebook. My second YouTube channel is titled 'Walks with Olly'.

4 thoughts on “Cleveland Way: Day 1”

    1. Thank you, Jon. It’s probably worth exploring at some point. The next couple of days would be spent very much on-the-moor. But I still feel like I only really scratched the surface of the North York Moors.


  1. Oh Olly, I really understand those mixed feelings when starting out on a long trek and feeling far from home, especially when things don’t go well at the start (such as difficulty finding a place to park). What a lovely gift your friend has given you in those letters – so thoughtful.

    Liked by 1 person

    1. Hi Ruth,
      I’m glad you also understand those feelings. I imagine they most be so common and yet, few talk about it. Are they boldly trying to look forwards and suppress the rest? What she did for me was unforgettable… One of the hardest feelings was driving 4.5 hours away from her and then not seeing each other for the next seven days! We both missed each other.

      Thanks for reading, Ruth.


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