Reasons to walk the Cleveland Way

By Mark Wright

The Cleveland Way has established itself as a firm favourite with Mickledore walkers. One of England’s original National Trails, this delightful 109 mile route runs from Helmsley, on the southern edge of the North York Moors, up to Saltburn-by-the-Sea, before making its way down the North Yorkshire coast to Filey. It’s an enchanting journey through two very distinct types of landscape – wild moorland and rugged clifftops.

Here we take a look at just a few of the elements that will ensure that time spent walking the Cleveland Way will prove an enriching and rewarding experience.

A Rich History

The Cleveland Way begins in the charming market town of Helmsley with its medieval castle dominating the skyline. You can explore the castle’s magnificent walls and immerse yourself in the tales of its historical significance, particularly its role in the English Civil War.

Throughout the Cleveland Way you will encounter remnants of ancient times such as the impressive ruins of Rievaulx Abbey, an eloquent testimony to the once-flourishing power of medieval monasticism.

The haunting beauty of Whitby Abbey, perched on the cliffs overlooking the town, invokes a sense of awe and mystery. This stunning gothic abbey served as inspiration for Bram Stoker’s Dracula.

The Cleveland coastline is peppered with picturesque villages such as Staithes and Robin Hood’s Bay, telling stories of maritime history, smuggling, and the toil of fishing communities. These quaint villages are living relics of a bygone era, their cobbled streets and historic buildings echoing with tales of the sea.

Natural Beauty

The Cleveland Way showcases the raw and untamed beauty of the North Yorkshire countryside and coastline, from the sweeping expanses of the North York Moors draped in vibrant heather to the rugged cliffs towering above the sea. Each day unfolds like a new chapter, serving up panoramic views and ever changing scenery that will impress even the most travelled of walkers.

Sutton Bank provides a panoramic viewpoint that is simply breathtaking. Here, walkers are rewarded with stunning views that stretch as far as the eye can see. The vastness of the landscape is a testament to the beauty and splendour of the English countryside.

The trail’s coastal stretches are without a doubt a highlight, where walkers are treated to awe-inspiring views of the North Sea. The dramatic cliffs stand guard over secluded coves and pebble beaches, creating a picturesque contrast against the endless expanse of the sea.

It’s evident that nature thrives along the Cleveland Way. From seabirds nesting on the cliffs to the rich flora and fauna of the moors, the trail is a haven for nature enthusiasts and photographers seeking encounters with red kites, fallow deer, puffins, seals, and other coastal wildlife.

Cultural Heritage

The Cleveland Way features a number of significant historical landmarks and museums. Visitors can explore sites such as the aforementioned Helmsley Castle, Rievaulx Abbey, or the Whitby Abbey Visitor Centre, where history comes alive through exhibits and guided tours, offering deeper insights into the region’s cultural heritage. Another landmark on the trail is the Captain Cook Monument commemorating the renowned British explorer, Captain James Cook, and you can explore the maritime heritage of the area at the Captain Cook Memorial Museum in Whitby.

The trail winds its way through welcoming towns and villages, offering walkers a chance to interact with locals. Whether it’s a word or two in the village shop or a friendly chat in a traditional pub, these encounters offer insights into the region’s traditions and local way of life.

Immersing yourself in local traditions and cuisine is an integral part of the cultural experience. Whether savouring traditional dishes in local eateries or exploring community projects walkers have the opportunity to taste the flavours and embrace the customs that define the area’s cultural identity.

Peace and Tranquility

A long distance trail such as the Cleveland Way not only offers physical exercise but also a mental escape. It provides opportunities for introspection and creates space for personal reflection amidst the beauty of the surroundings. The soothing influence of nature, moments of solitude, and the rhythm of walking can be profoundly therapeutic. Walking the trail becomes a meditative experience.

The calming effect of the moorland’s vast expanses or the tranquil sounds of waves crashing against the coast offers a sense of peace and tranquility, the benefits of which are not to be underestimated.

Plenty of Choice

Seasoned walkers can choose to walk the full Cleveland Way from Helmsley to Filey in a choice of 7, 9 or 11 days. For those with a little less time to spare or who perhaps aren’t quite ready to take on 109 miles in a single trip, we also have 3 shorter holidays to choose from, each walked over 5 days.

You can walk the 60 mile Moorland Highlights, from Helmsley to Saltburn-by-the-Sea. Then we have the Coastal Highlights, walking 51 miles from Saltburn-by-The-Sea to Filey. Walking the Moorland and Coastal sections over separate holidays will for many be the ideal way to complete the Cleveland Way. Finally, for those looking for a condensed moorland and coastal experience, we offer our Combined Highlights holiday, walking 62 miles from Osmotherly to Robin Hood’s Bay. Each of our holidays on the Cleveland Way have dog-friendly options.


The Cleveland Way National Trail is more than just a walk; it’s an immersive experience that connects you with nature, history, and local culture. What we have laid out here are just a handful of the many reasons why anyone seeking adventure, exploration, and a deeper connection with the natural world should consider walking the Cleveland Way. Could it be your next great outdoor adventure? For further information on the Cleveland Way and to book your 2024 adventure email u[email protected] or call us on 017687 72335 to speak with one of our walking holiday experts.

Client Feedback

Working with everyone at Mickledore was a FANTASTIC experience! It could not have gone any better. Everything was top-notch, and every penny I spent was worth it. You all were responsive, professional, and efficient. Very impressive. I’ve already recommended Mickledore to several friends and fellow walkers!

Cleveland Way, July 2023
Read more >

Like a dream. You nailed so many things and made our trip one we will never forget. Will recommend you to all and think you’re an amazing company. No issues the entire time! We switched our dates and was done easily. I cannot believe how smooth it was and that we didnt need to bother you. Coming all the way from America we thought we would need more help. Will tell lots of people about you and the team

Hadrian’s Wall Walk, June 2023
Read more >

This was my third holiday with you. I have been pleased with your service, level of support, the B&Bs you choose and the helpful voice that is there when I phone you. I also think your holidays are good value for money. Thank you

Coast to Coast, June 2023
Read more >