A SUPERB WALKING CHALLENGE ON THE CLEVELAND WAY near TEESSIDE

For the past few years me and some mates have done a walking challenge in memory of a good friend who passed away recently. We live in Teesside and last year we done the fabled Lyke Wake Walk – a 40 mile walking challenge across the North York Moors in 16 hours.

For this years challenge we done another local route and a bit shorter one at 26 miles, starting in the village of Osmotherley and walking the Cleveland Way right to the iconic landmark of Roseberry Topping. It’s a walking challenge I’ve wanted to do for a long time, as you can pretty much see the full route on the Cleveland Hills from where I live – but always felt it was too long – but after the 40 mile Lyke Wake Walk it seemed it would be a doddle haha. If you want a good walking challenge in this area then this route is a really good one – testing but doable! Read on to learn more about our walk.

Map route from Osmotherely to Roseberry Topping:

Here’s the full walking route along the Cleveland Way, west to east, from Osmotherly to Roseberry Topping. It’s a hilly walk with plenty of ups and downs to add to the challenge – and as you are on the Cleveland Hills you get some of the best views in North Yorkshire! The full interactive map route can be found on the button above.

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PHOTOS OF OUR WALK:

We get dropped off in a car at the lovely village of Osmotherly and head straight onto the Cleveland Way. Once you are up and out of Osmotherley, the North York Moors really open up into a wide expanse. Here you can see the well marked Cleveland Way, with Roseberry Topping right in the far distance. We’ll be tracking the hilly summits to the right of the photo.

The Cleveland Way is a well marked path for most of it with plenty of signage to keep you on track. 

Looking back at the terrain we’ve covered on the hilly peaks.

The Cleveland Hills arent the tallest peaks out there – but on this walk there are plenty of ups and downs and the total ascent on this route is just over 4,500ft – which is a 1000ft more than the summit of Ben Nevis! 

The distinctive rocky outcrop of the Wainstones – a good place to rest, eat, air the feet and change the socks (one of my best tips on long walks – keep the feet dry by changing socks regulary!) 

The walk up until this point has been really enjoyable and scenic. Just after here as you cross Clay Bank road to Kildale it starts to get a little challenging, mainly because you start to head away from your view of Roseberry Topping which is to the left of this photo – but the path takes you right. One moment you think your getting close to the target – then it’s further away!

A photo of us at around the 2/3 mark at Cockayne Ridge, a good place to stop and get some fuel into you. From here it’s almost as teh crow flies to Rosebrry Topping.

The path gets a bit monotonous for a few miles here – with not much in terms of views. I always find these sections of long walks the most challenging as the view rarely changes so you dont feel like you are getting anywhere

Roseberry Topping comes into view again – a welcome sight! 

For a short while we walk on a quiet road before dropping into Kildale and then heading back up towards Captain Cooks monument. 

Another welcome pit stop and Rosebrry Topping is not that far away now. I’ve walked from here to Rosebrry Topping loads of times and know we’ve only maybe got 45 mins or so left

It’s getting towards sunset time now so we’ve timed thsi walk just right!

The final stretch. Roseberry Topping is usually a doddle to walk up – but with 25 miles done it’s very heavy going on the legs. Some people we pass must think we are really unfit the way we walk up it with out walking poles like it’s a big mountain haha – little do they know we’ve been walking over 12 hours

We’ve made it! Just over 25 miles and 12.5 hours – that one’s for you Wrighty!

Roseberry Topping is the peak I’ve walked up the most – and this one must go down as the most special and rewarding. If you are looking for a good walking challenge then I highly recommend this route! Now it’s a small matter of making it back down to the nearest pub – which is the Kings Head Inn at the foot of Roseberry Topping. We enjoy a pint, some food and await our lift home!