The Cleveland Way - Day 1 (Helmsley to High Paradise) - May 2023

We had two days booked off work in May and planned to walk a couple of sections of the Cleveland Way, a 109 mile trail that runs inland through the North York Moors National Park and along the East Coast from Saltburn to Filey. After deciding to attempt some long-distance walking in 2024, we have been using the odd long weekend to get used to walking a reasonable distance across several days, carrying our packs. Unfortunately we did not have time for the whole trail, but plan to undertake it in full next May, all being well.

I should make it clear that the word ‘novice’ appears all over this blog for a reason. My fitness levels are pretty crap, I haven’t hiked with anything more than a day sack since doing the Duke of Edinburgh Bronze Award and that was more years ago than I care to remember, and I’m not even sure I can properly pitch a tent. These walks are new to us (and our little dog) and we are dipping our toes in at the moment, figuring out what works for us (and what doesn't) before committing to a full long-distance hike. Let’s just call the hiking journey a work in progress…

We started our walk in Helmsley, parking in the overflow carpark and taking the obligatory photograph of the stone seat at the start of the route (pictured). I purchased two 24-hour tickets for the same day, in the hope it would be fine to stay for 48 hours (it was). I still have no idea if we were just lucky with this and I was anxious about getting a parking fine, so next time I would plan the parking a little better. For example, we both agreed we would prefer walking towards the car as opposed to away from it, parking it somewhere pre-arranged or at a long-stay carpark.

It was a perfect day for walking, with a cool breeze but otherwise dry and sunny. The first part of the walk was familiar to us, as we often do a day walk from Helmsley to Riveaulx Abbey, stop for lunch in Riveaulx Abbey and then walk back again. The walk towards Riveaulx is easy, with just one short climb up woodland steps. The rest of that section is largely flat or downhill, on a clearly marked, wide path.

As we visit Riveaulx a lot, we decided not to add the extra distance onto our walk, but I would highly recommend it if you haven’t been before, particularly if you have English Heritage membership or can get a monthly membership to make use of while you’re in the area. It will only add about half a mile and the dramatic abbey ruins provide a quiet spot to sit with a coffee and take in an awe-inspiring piece of history.

The next part of the Cleveland Way involves a stretch of country road. We saw very little traffic, but I know from watching YouTube videos (shoutout GENeration Xplorers) that is not everybody’s experience. Light traffic or not, we were still pleased to be off the road and back on the main trail, a wide gravel path, with some tree coverage providing welcome relief from the sun.

It was at this point we took our first wrong turn (pictured). It is incredibly difficult to go wrong on this section of the walk, but we made the rookie mistake of not double checking when the road forked into three possible options. Despite having a paper map, the route plotted on our OS app and a compass, we still managed to veer off in the wrong direction by relying on that well-known navigation tool, ‘gut instinct.’

Although annoying, this was a safe and drama-free way to learn a valuable lesson about checking our route when unsure. On realising we had gone wrong, our map proved very useful as we were able to plan a detour through Old Byland instead of retracing our steps. We followed an alternative route to get us back onto the Cleveland Way, after stopping for a quick packed lunch just outside Old Byland. The detour meant we lost some of the more spectacular climbs and ended up on a long stretch of tarmac road walking. This, combined with the tractor making regular trips alongside us to take manure from one point to another, just served to hammer home the point: read the bloody map.

Eventually, we rejoined the Cleveland Way and climbed towards Sutton Bank. We have done the path that takes you to The White Horse of Kilburn several times and decided not to take in this optional extra. If you are in the area for the first time, detouring to the White Horse and back is a very easy, flat walk and worth it for the gliding club and views if visibility is good and your legs are feeling up to it. If you have a longer walk planned than we did for Day 1, Sutton Bank visitor’s centre is a good place to stop for refreshments.

The last section of the walk was beautiful, with glorious views and a final gentle climb through Hambleton Woods. We had booked to stay at High Paradise Farm, a popular spot with walkers on the Cleveland Way due to the fact it is on the trail. There is a lovely café, and we purchased a welcome cold beer before tucking into the pasta pouches we packed for the trip. We slept very well.

Pros: Well-marked trail. Easy to navigate throughout. List-ticking views. Mixed terrain (gravel paths, farmland, woodland) offered good variety. Several points to stop for refreshments. The pooch (pictured) enjoyed it (lots of sniffs).

Cons: Working out parking options was a pain. Some road walking.

Next Time: Find alternative parking options. Do the correct route!

Distance: 14 miles.