A walk of two distinct halves: sweeping moorland and spectacular coast. The Cleveland Way blends the inland beauty of the North York Moors with the drama of Yorkshire’s cliff-edged shoreline.
Highlights
The Cleveland Way offers remarkable variety, from the peaceful uplands of the North York Moors to the ever-changing skies and craggy coastline of Yorkshire. Beginning in the market town of Helmsley, the first half of the trail meanders through woodland, ancient abbeys and wide moorland ridges. The second half opens out onto the coast, where you follow clifftop paths above the North Sea, passing fishing villages, hidden bays and wide beaches. This is a route for walkers who appreciate contrast—quiet, expansive moors one day and the buzz of seaside towns the next. It’s a journey shaped by heritage and landscape, with plenty of rewarding overnight stops along the way.
The Cleveland Way begins in the traditional market town of Helmsley, winding its way through the North York Moors National Park before reaching the dramatic North Sea coast at Saltburn. From here, it follows the coastline southwards, hugging towering cliffs and dipping into charming fishing villages such as Staithes, Robin Hood’s Bay and Runswick Bay, before finishing at the historic seaside resort of Filey. Along the route, walkers encounter a rich mix of wild moorland, heather-covered hills, and coastal headlands, punctuated with ancient sites. The terrain is varied but manageable, with well-maintained paths across undulating countryside and cliff-top trails offering sweeping sea views. Though some sections can be windswept and exposed, the walking is never overly strenuous, making this a satisfying yet accessible long-distance path. Whether crossing purple moor or descending into a bustling harbour, each stretch offers its own distinctive character and sense of place.
What makes the Cleveland Way particularly striking is its dramatic contrast — no other National Trail in England transitions so seamlessly from heather moorland to rugged coastal cliffs. You begin immersed in the sweeping solitude of the North York Moors, where curlews call across the open hills and ancient stone crosses mark the way. Then, without warning, the trail tips you onto the edge of the sea, revealing some of Yorkshire’s most iconic coastal views. There’s an extraordinary sense of history underfoot too: from the haunting ruins of Rievaulx and Whitby Abbey to the storied smugglers’ coves that line the coast. Literary connections run deep here, with Bram Stoker drawing on Whitby’s gothic atmosphere to inspire Dracula. This route offers not just scenic grandeur, but a walk through centuries of culture, folklore and resilience. Whether you’re drawn by the wilderness or the waves, the Cleveland Way captures the spirit of northern England in all its rugged beauty.
Choose Your Walk
From £1,475 Per Person
From £1,370 Per Person
Looking for different mileages or a different number of nights? Please contact us to discuss how our itineraries can be adjusted to meet your specific needs.
4.8/5 based on 43 reviews
"Celtic Trails sort out the practicalities so you can focus on and enjoy the walk and rest in between. Feel a great sense of achievement from this holiday. The contrast between the moors, woods and coastline was fabulous. We wish we'd scheduled a rest day."
"Excellent"
"You were prompt and friendly in your responses and very easy and pleasant to work with."
"Celtic Trails were flexible, helpful, reliable and efficient"
"A holiday company which provides excellent, personal customer service from enquiry, to booking, to provision of walk information with knowledgeable and helpful staff. Thank you again, Penny, for making the arrangements for our holiday and ensuring that everything went smoothly."
"Celtic trails are very professional and well organised"
"As a single walker I feel really safe and well looked after and I love the flexibility to book rest days. A walking holiday with no worries, I can just wake up and start walking to my next destination and arrive happy and you can be sure to stay in lovely accommodations. Thank you Celtic Trails."
"Perfect and very friendly and swift service."
"Celtic Trails are always a pleasure to deal with. The Cleveland Way is the longest walk I have done and was a true challenge for me which I am so pleased and proud to have risen to."
We seek out the best accommodation of its type available
A historic Victorian resort town as well as a working fishing port, complete with the ruins of the imposing abbey sat on the hill overhead. The seaside town is a great place for eating out, from Michelin-starred gastropubs to one of the best fish & chip dinners available in the UK.
Walkers spend the night in Whitby on the Staithes section of the CLV1; let us know and we'll be more than happy to arrange an extra rest day to explore the area.
Looking for different mileages or a different number of nights? Please contact us to discuss how our itineraries can be adjusted to meet your specific needs.
Looking for different mileages or a different number of nights? Please contact us to discuss how our itineraries can be adjusted to meet your specific needs.
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