Cleveland Way
Self-guided walking holidays along the Cleveland Way. Accommodation, luggage transfer and custom holiday pack included.
Cleveland Way
https://dev.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 110-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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“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
“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
“The best hiking trail we have done, very lucky with the weather, but some excellent hiking, a good mix of easy hiking and harder section. Visited some very nice towns, and excellent moorland and coastal hiking. Great hiking, superb scenery, some very good meals out, some very good accommodation. Will absolutely book with you again, this was our 5th, I think, and best.”Miss Steggall, 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 was great - the map booklet, luggage transfers, taxis and accommodation. Really enjoyed being out walking all day.”Mrs Jones, UK
“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
“Really good, it all went very well, organisation was perfect, no complaints! Great scenery, lovely walking, everything went to plan, so we never really thought much about the organisation!”Mr Astle, 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
“This was the best long distance trail to date that I have had the pleasure of walking. The scenery was amazing – countryside, moorland and coast all in one package. Challenging in places but doable.”Mr Wilson, UK
Dog friendly