Cleveland Way: 50 Years of Countryside & Coast

After walking the South West Coast Path and Hadrian’s Wall Path last year I thought I had experienced the crème de la crème of England's long-distance walking trails. I didn’t once imagine that the unassuming Cleveland Way would compare to those I had previously walked ... I was wrong.

Caitlin from the Absolute Escapes team on the Cleveland Way
Caitlin from the Absolute Escapes team on the Cleveland Way

This wonderful National Trail climbs around, through, and over moorland, then along the north east coast of England.

Starting in the attractive market town of Helmsley and ending in Filey you might be asking yourself how this path’s main attraction can be both vibrant moorland and dramatic coast. As the crow flies, Filey is 35 miles east of Helmsley, so you would be correct to question this, however the Cleveland Way takes a beautiful, memorable and stunning horseshoe shaped detour of 109 miles (175 km), skirting around the North York Moors National Park and hugging the winding coast to Filey.

Beach huts near Whitby
Beach huts in Whitby

You are probably still wondering what makes the Cleveland Way so special and why, out of 15 National Trails, this should be your next walk?

A Momentous Age

The Cleveland Way started as a twinkle in the eye of the Middlesbrough Rambling Club who, in the 1930s, mapped out a trail that would take them over the North York Moors and onto the East Coast of England. It wasn’t until 1969, however, that this trail was officially recognised as a long-distance path.

On Friday 24th May 2019 the Cleveland Way will be celebrating its impressive age of 50 years. That milestone should be a good enough reason to get you stomping along here!

Overlooking Staithes
The village of Staithes

Real Sense of History

The very first section of this path holds an impressive amount of history waiting to be explored, starting at Helmsley Castle which is located in the village centre. Dating back to the 12th century, this once mighty medieval fortress is a great spot to swing by before commencing the walk.

Helmsley Castle
Helmsley Castle (Photo credit: Andrew Wilkinson / Flickr)

Those interested in history will be delighted to learn that not too far from Helmsley is Rievaulx Abbey. Located half a mile from the official trail, you will find ruins of an impressive 12th century Cistercian Abbey which sits in the woods of the Rye Valley.

I recommend taking this rewarding detour and, as you do, bear in mind that you are following the footsteps of Saint Aelred of Rievaulx, one of Yorkshire’s most famous abbots. Making this mini-pilgrimage from Helmsley to Rievaulx ensures the start of your walk is peaceful and relaxed, and provides the perfect opportunity to appreciate your surroundings whilst preparing yourself for the next hundred miles.

Rievaulx Abbey
Rievaulx Abbey (Photo credit: Michael D. Beckwith / Flickr)

Closer to the other end of the trail is the impressive Whitby Abbey. Perched high on a cliff overlooking the hustle and bustle of this popular holiday destination, this medieval abbey famously inspired Bram Stoker’s horror classic Dracula. A fantastic piece of gothic architecture, this is a highlight for those interested in design but also history, with remains that date back to the 13th century.

View across Whitby with Whitby Abbey in the background

Moors & Shores

The beauty of the Cleveland Way is that it encompasses varying scenery, and is often thought of as two separate and contrasting sections of trail which makes for an interesting and rewarding walking holiday.

The first 60 miles focus on encircling the largest open moorland in England - the North York Moors. This peaceful area offers the opportunity to spot wildlife such as red grouse and curlews. The moors are also famous for hosting the largest area of heather moorland in England, so walking through this at the right time of the year, ideally in September, will reward you with inspirational views of vibrant heather.

North York Moors
North York Moors National Park

After reaching the top of the Roseberry Topping and passing Captain Cook’s Monument, the path starts its approach to the North Sea. The sight of the wild waters offers a very welcome change of landscape and a gentle introduction to what lies ahead.

Saltburn-by-the-Sea marks the beginning of the contrasting second stage of this trail. The rest of the path hugs the rugged and endearing Cleveland Heritage Coast 40 miles south to Filey, passing old fishing villages and lively coastal towns.

This ever-changing backdrop makes walking the entirety of the trail an interesting and enjoyable experience which is not to be missed.

Runswick Bay
Runswick Bay

Coastal Communities

A strong contender for my highlight of the trail was the quaint coastal village of Staithes. Nestled under towering cliffs, this picturesque old village is full of life, talented and friendly artists, charming alleyways, and hundreds of singing seagulls!

Your afternoon can slip away very quickly here so ensure you make the most of it by visiting Dotty's Vintage Tea Room, before crossing the road to The Royal George where you can enjoy a drink and watch the world pass by, bumping over the cobbled streets.

Caitlin from the Absolute Escapes team in Staithes
Caitlin from the Absolute Escapes team (left) in Staithes

Another charming coastal village that made a mark on me is the quaint village of Robin Hood’s Bay, located 26 miles north of the finishing point. This fascinating and picturesque old fishing village is full of narrow, twisting cobbled streets and alleyways. Enjoy roaming the streets and visiting the independent cafes, restaurants and shops that make this village hum with activity.

Robin Hood's Bay
Robin Hood's Bay (Photo credit: Matthew Hartley / Flickr)

The Cleveland Way will lead you through this beautiful untouched north English landscape where you can meet the locals, stop off in picture-postcard seaside villages, and discover its fascinating history.

The path is brilliantly way marked, easily accessible via public transport, and offers the opportunity to extend onto the Coast to Coast long-distance trail which runs from Robin Hood’s Bay to St Bees.

Caitlin Richmond 
P.S. If you’d like to experience the Cleveland Way for yourself, Absolute Escapes offers self-guided walking holidays along the trail. Our packages include accommodation, daily baggage transfers, guidebook/map, and a full information pack. Send us an enquiry - we’d love to help you plan an unforgettable walk.
Cleveland Way waymarkers
Cleveland Way waymarkers
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