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
“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 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
“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
“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
“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
“Everything was great - the map booklet, luggage transfers, taxis and accommodation. Really enjoyed being out walking all day.”Mrs Jones, 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
Dog friendly