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 £402 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 £798 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 | £798 | |
| CLEVW2 | From Helmsley to Filey | 7 days walking | £1056 | |
| CLEVW3 | From Helmsley to Filey | 9 days walking | £1308 | |
| CLEVW4 | From Helmsley to Filey | 10 days walking | £1434 |
| Code | Tour | Duration | Price per person | |
|---|---|---|---|---|
| CLEVWSB | From Helmsley to Osmotherley | 2 days walking | £402 |
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“A well organised holiday walking a lovely route.”Mr Whiley, UK
“Everything was great - the map booklet, luggage transfers, taxis and accommodation. Really enjoyed being out walking all day.”Mrs Jones, 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
“This was one of the most enjoyable long distance walking holidays yet! We barely needed the handbook and maps, it was so clearly signed. We have always found the Contours service reliable.”Mrs Burke, UK
“Thank you for everything. We have been most impressed with our booking with Contours doing the Cleveland Way last week – every accommodation was perfectly situated, clean, welcoming and excellent food. Thank you for your excellent organisation, we have felt very comfortable with all the arrangements and could not fault anything. Last year we did a Camino walk booking with a Spanish company that felt badly short at times on communication so it really highlighted to us how booking with Contours gives us much more peace of mind.”Mrs Steele, UK
“Everything went to plan, even the weather!”Mr Newton, UK
“We were very pleased with all of the accommodation booked for us and the information provided, The taxi driver were very good and arrived in time if not before.”Mr Gamble, 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
“Hampered by an infected and sore foot, which was obviously no fault of Contours, but it was still a good experience. Would have been excellent had I been fit, but that is another story.”Mr Spencer, UK
Dog friendly