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
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 | £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 |
“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
“Extremely beautiful walk.”Dr Hicks, UK
“It was absolutely perfect, I enjoyed every minute. I have already recommended that particular holiday, and Contours in general, to many friends. Planning to book with you again in 2022.”Mrs Allen, USA
“Lots of variety with moors and coast. All ran smoothly.”Mrs Cartledge, UK
“Good weather, lovely scenery and paths, niggles in taxi arrangements but overall a lovely holiday. Lovely gentle rolling wolds, very well signed, quiet.”Dr Chatfield, 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
“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
“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
“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