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

The whole trip was just fantastic, I have recommended it and you to so many people. All we had to think about was the walk each day and what we were going to see. The organisation of it all was faultless and left us to just enjoy it all.

West Highland Way, September 2023
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Your staff seem really enthusiastic about your holidays and are very helpful when needed. It seems that our enjoyment of our holiday is important to your staff.

Westmorland Way, September 2023
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The staff are very friendly and efficient, the info packs with supporting info are great, the accommodation options are varied and excellent.

Lady Anne’s Way, August 2023
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