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 £390 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.
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 £760 per person
Book your self-guided walking holiday along the Cleveland Way. This holiday option 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 | £760 | |
| CLEVW2 | From Helmsley to Filey | 7 days walking | £1005 | |
| CLEVW3 | From Helmsley to Filey | 9 days walking | £1245 | |
| CLEVW4 | From Helmsley to Filey | 10 days walking | £1365 |
| Code | Tour | Duration | Price per person | |
|---|---|---|---|---|
| CLEVWSB | From Helmsley to Osmotherley | 2 days walking | £390 |
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“Great walking. Good scenery. Met many friendly people along the way.”Mr Calvert, 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
“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
“Wonderful contrasts of landscapes, and similar to our previous trips, luggage transfers worked well, variety of accommodations appreciated, and a good time had by us.”Ms Miller, USA
“I was lucky with the weather. I had only one day with rain and two days with some drizzle. The views were great. And I met interesting people. The Cleveland Way is an excellent mixture of moorland and coastal walk with some places of history, e.g. Rievaulx Abbey, Whitby Abbey. Again the team of Contours did a good job. It was my walk no 14 with Contours!”Mr Witzel, Germany
“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
“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
“The walk was the best we have done so far with Contours. The walk itself was varied, challenging in places, and it obviously helped that the weather was nearly perfect. The instructions from Contours were excellent as always and the accommodation was mostly good or better. The baggage transfers worked without a hitch.”Mr Gill, UK
“with whom else would I book with”Mr Van Den Busch, Germany
Dog friendly