We’re thrilled to see one of our self-guided walking trips featured in Country Walking Magazine on Live for the Outdoors, with writer Nick Hallissey walking the Cleveland Way from start to finish. His in-depth account follows our Cleveland Way itinerary from Helmsley to Filey, capturing exactly why this National Trail stands out as one of England’s most varied long-distance walks. 

Encircling the North York Moors National Park, the Cleveland Way packs an astonishing amount into 110 miles - and this feature brings the route to life, day by day. 

Read the full Country Walking Magazine article here >

A Long-Distance Walk Like No Other 

Many trails are defined by one standout feature - the Cleveland Way refuses to choose. In Nick’s account, forested ravines, open moorland, rolling ridgelines, sweeping cliffs, sandy beaches and classic seaside towns unfold in constant succession, often within the same day. 

Walking clockwise, the route traces a natural arc along the Hambleton Hills, across the Cleveland Hills and down the Yorkshire coast. Highlights include the ruins of Rievaulx Abbey, the vast views from Sutton Bank, ridge walks past Carlton Bank, Cringle Moor and the Wain Stones, and the unmistakable silhouette of Roseberry Topping - climbed in both evening light and early morning calm. 

Midway through, the trail meets the sea at Saltburn-by-the-Sea, shifting into superb coastal walking shared with the England Coast Path. Fishing villages like Staithes, dramatic clifftops, hidden beaches and the legendary arrival into Whitby follow, before a final, wildlife-rich stretch to Filey that leaves Nick wishing the journey wasn’t over. 

Walking the Cleveland Way with Macs Adventure 

Throughout the article, Nick highlights the ease of walking the Cleveland Way with Macs Adventure. Accommodation, luggage transfers, route notes and maps are all seamlessly organised, allowing him to focus purely on the walking. Each evening, his bag is waiting at the next carefully chosen stay; each morning, the route is ready to go. 

It’s this combination of exceptional organisation and extraordinary landscape that leads Nick to describe the Cleveland Way as one of the most rewarding long-distance walks he’s ever experienced. 

Read the Full Feature 

This summary offers just a taste of a richly detailed and beautifully written account. To follow the Cleveland Way day by day - and to experience its full variety, character and sense of place - read the full article on Live for the Outdoors, from Country Walking Magazine. 

And if this story has sparked your interest, explore our Cleveland Way self-guided walking holidays to see how you could experience it for yourself.