Planning the Cleveland Way for late August 2026

I’m goign to shift the Peaks of the Balkans trip back a week or two to get cheaper flights, a quieter trail, and less competition for guesthouses.

That means I’ve got a window to fill for the end of August, so I’m looking at fitting the Cleveland Way in. I’ve been looking at the trail for a few years and I still haven’t explored much in Yorkshire at all, despite having lived in Sheffield for a couple of years in the early 2000s.

It also means this will be the first trail I’ll be researching for Trail Almanac in person and in earnest.

The Cleveland Way is 109 miles / 176 km route and is something of a trail of two halves; the first being a loop around the North York Moors, and the final stretch taking you down the coast to a little south of Scarborough. Neither are areas I know at all.

Late August is supposed to be peak heather season too, though I’m not sure how the summers drought might affect that.

So, to planning.

Transport

The trail starts in Helmsley, about 25 miles north of York. You’d think that would make the journey straightforward. Just get the train to York and jump on a bus. Except, that is, for the fact that those 25 miles take at least an hour and a half on the local bus service, and the fact that a standard return fare from Chichester, where I’ll be starting the journey, is upwards of £150 for a 14 hour round journey (even with the Trainline confidently announcing it was savings me £116.60) followed by a 3 hour round journey or the 25 mile bus ride. What a stitch. There’s no National Express option joining Chichester to York either.

So there’s the driving option. At 300 miles each way that puts fuel at £120 plus about £30 parking for the week I’ll be out, and we’re saving over public transport. As a country, we surely need to address that.

Either way, we still need to deal with public transport for the Filey (finishing trailhead) to Helmsley (over 3 hours) or York (over 4 hours) stretch. Hopefully by the time that comes around, I’ll be in holiday mode and won’t care.

Stages

I’m looking at a 7 day plan for this, carrying capming gear but mainly using organised campgrounds with a couple of hostels thrown in. It looks something like this atm:

Stage 1: Helmsley to High Paradise Farm, 17.4 km

Keep it shortish the first day after a long drive. I can usually do 18 km ni 4 hours but terrain will obviously be a factor.

Accommodation: https://www.highparadise.co.uk/camping.html.

Cleveland Way Walkers. No need to book, just turn up, but you must arrive on foot. Send us a text on the day you are coming so we know to look out for you: 07739498255 (£15.00 per person per night)

Stage 2: High Paradise Farm to Lordstones Country Park, 23.9 km

Two options for destination toady. Either Beak Hills Farm:

To book accommodation at Beak Hills Farm, you can call us on 01642 778371 or email us at [email protected]
Adult per night: £5

Or Lordstones Country Park:

£26

The difference other than price is obvsiously distance either side. From High Paradise Farm to Lordstones is 23.9 km, and from there on to Park Farm is 19.3 km.

From High Paradise to Beak Hills Farm is 27.3 km plus a 1 km diversion. On to Park Farm from Beak Hills is 17.7 km plus the 1km back to trail.

Stage 3: Lordstones to Park Farm, 21.6 km

Kildale Camping and Barn at Park Farm is tonight’s stop.

How do I book?
Email us using our contact form or telephone 01642 722847
£12

Stage 4: Park Farm to Magpie Wood, 25.7 km

No website for Magpie Wood though there’s a FB page). I’d expect it to be about £20 to pitch and to book, it’s either 07444 288058 or [email protected].

Stage 5: Magpie Wood to YHA Whitby, 28.7 km

It’s apparently 43 quid to stay in a YHA in 2026. WTF? Oh – that’s right, only if you stay on a Friday or Saturday night. £33 otherwise. As if I’ll have the faintest idea what day of the week it is by then. I’m not even going to link to them. Oh and from 1 Sep it’s £23 midweek!

One more option. There’s a campground right by Whitby Abbey. It advertises a dangerously close, 5 min walk from Abbey, beach and brewery. Abbey Farm Showfield, £25 a night including weekends.

Stage 6: Whitby to Hulleys Campsite, 24.6 km

I was expcting to go all the way to Scarborough this day until I chanced across this campgroud almost by accident. Looks like a better distance split for the last couple of days.

There’s no availability for the night I expect to arrive on pitchup but I’m hoping I can call it in on the day.

Stage 7: Hulleys to Filey Brigg, 27.5 km

And this is where we’ll end. There’l l be an additional 2.5 km to the station from the end of the trail. No accommodation expected. I’ll return to Helmsley or stop in Scarborough overnight, I imagine.

Supplies

Although it’s good to know a full resupply is possible in Helmsley in case I forgot my tea bags, I’ll obviously arrive fully loaded. After that, we have:

Osmotherley: Three pubs serving food, a very small village shop and a small café.

Lordstones Country Park: shop and cafe

Great Ayton: Full resupply, off-trail

Guisborough: Full resupply, off-trail

Saltburn-by-the-Seab: Shops, cafés, pubs

Runswick Bay: Cafe and pub, no shop.

Whitby: All options

Robin Hood’s Bay: Village shops and pubs

Scarborough: All options

Gear

Despite immediately following England driest July on record, I don’t think I can bring myself to take my single-wall 1p tent and down bag. So I’ll be with the Durston X-mid 2. It’s actually been kind of a pain to find spots for it in tight confines. It’s only been out with me once so far, and that was on a week long section of the desert section of the PCT earlier this year. It was a annoying getting it up in a combo of high winds and soft sand, and there it was tight to say the least in some the spots I found in the canyons north of Scissors Crossing. But this will be largely organised campground living, so that shouldn’t be an issue. It should be easier to keep myself and my bag dry if it’s wet or condensation-y though.

I’ll be carrying this lot.

The Need to Locate Pronto List

90% of my stuff is still in storage so I need to get in there to find:

• Headtorch