Cleveland Way
Self-guided walking holidays along the Cleveland Way. Accommodation, luggage transfer and custom holiday pack included.
Cleveland Way
https://www.contours.co.uk/cleveland-way
A self-guided walk around the North York Moors National Park and the Cleveland Heritage Coast.
From £422 per person
Take a self-guided walking holiday along the Cleveland Way, a walk of stunning contrasts. Beginning in the old market town of Helmsley, the Cleveland Way traverses the western escarpment of the North York Moors to the coast at Saltburn-by-the-Sea, before following the Cleveland Heritage Coast to the Victorian town of Filey.
While walking through the Moors, the trail traverses woodland, green dales and heather moorland. This section is packed with historic interest, including the iconic White Horse of Kilburn. The coastal section then follows high cliffs, sandy bays and wooded wykes. Picturesque fishing villages pepper the trail, as well as the famous port of Whitby. Overall, the Cleveland Way is an incredible walking trail filled with intrigue and beauty.
We offer multiple holiday options along this trail. If you wish to experience the entire trail, simply select the first option from the list below.
Dogs are welcome on select routes along this trail. Look for the pawprint icon when choosing your holiday.
We also organise trail running holidays along this route. Find out more.
From £846 per person
The Cleveland Way spans 111 miles, from Helmsley to Filey. This self-guided walking holiday explores the entirety of the National Trail, from the tranquil beauty of the North York Moors National Park to the bustling fishing ports of the Cleveland Heritage Coast.
There is plenty of spectacular scenery and amazing history to discover along this 109-mile walking trail, with something new to take in at every turn. As the landscape changes from heather-clad moors and green dales to sandy beaches and breezy clifftops, the walk visits a range of old market towns and fishing villages, each boasting their own unique character and warm welcome.
| Code | Tour | Duration | Price per person | |
|---|---|---|---|---|
| CLEVW1 | From Helmsley to Filey | 5 days walking | £846 | |
| CLEVW2 | From Helmsley to Filey | 7 days walking | £1119 | |
| CLEVW3 | From Helmsley to Filey | 9 days walking | £1386 | |
| CLEVW4 | From Helmsley to Filey | 10 days walking | £1520 |
| Code | Tour | Duration | Price per person | |
|---|---|---|---|---|
| CLEVWSB | From Helmsley to Osmotherley | 2 days walking | £422 |
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“Just a quick note that our Cleveland Way walk booked through Contours was absolutely great, assisted by some great weather it must be said.”Mr Flather, UK
“Well organised, good accommodation and places to eat nearby. Good taxi transfers. Stunning scenery. I enjoyed it all for different reasons. Stages 1 & 2 easy walking with good views, stage 3 more challenging but again some great views made it worthwhile.”Dr Bowman, UK
“Lots of variety with moors and coast. All ran smoothly.”Mrs Cartledge, UK
“The holiday far exceeded my expectations. The accommodation was of the highest standard, the transfers were seamless and everyone involved from the accommodation staff and owners to the taxi drivers were extremely friendly and helpful. An extremely well planned and thought out holiday. I would recommend Contours Holidays and in particular, The Cleveland Way, to anyone. I will be planning another walk with Contours Walking Holidays shortly.”Mr Worman, UK
“Everything went to plan, even the weather!”Mr Newton, UK
“9 days of wonderful views and excellent B&Bs. We had a wonderful walk. Met interesting people on the trail and stayed in great places. Thanks to all the team for the perfect organisation. All taxi firms were excellent too.”Mr Darwen, UK
“Yes this was a great walk which I really enjoyed particularly the contrast between the moorland of the first few days and the coast thereafter. I really enjoyed it all and would do it all again although I might book an additional day in Scarborough next time to see round the town more. I think this holiday has something for everyone whatever type of walker you are.”Mr Madge, UK
“Four days good walking, with rain on one day only! Overall excellent. The Cleveland Way is an excellent walk. It can be demanding and the geography means accommodation can be widely spaced, making for some long sections. I've walked with Contours on five long distance walks now and have always been impressed by your professional efficiency.”Revd Moorhouse, UK
“The weather was very good apart from the last morning which made the whole walk stunning.”Mrs Edwards, UK
Dog friendly