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 £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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“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
“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
“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
“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
“Excellent choice of stays.”Mr Hallatt, 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
“As usual, the staging of the walk and the choice of accommodation were excellent.”Mr Calderisi, Canada
“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
“The combination of the moors and the sea coast is stunningly beautiful and provides great variety in the terrain and views. I am amazed at the amount of work that has gone into creating and maintaining the trail. This was my fourth holiday with Contours; I expect to book more in the future.”Ms Matthews, USA
Dog friendly