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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“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
“Everything went to plan, even the weather!”Mr Newton, 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
“As usual, the staging of the walk and the choice of accommodation were excellent.”Mr Calderisi, Canada
“with whom else would I book with”Mr Van Den Busch, Germany
“Great walking. Good scenery. Met many friendly people along the way.”Mr Calvert, UK
“The variety of landscapes on the Cleveland Way was really nice. The luggage transportation was flawless and the variety of lodging hosts and facilities was terrific. Well done!”Mr McCoy, USA
“A well organised holiday walking a lovely route.”Mr Whiley, 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
Dog friendly