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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“Four days good walking, with rain on one day only! Overall excellent. The Cleveland Way is an excellent walk. It can be demanding and the geography means accommodation can be widely spaced, making for some long sections. I've walked with Contours on five long distance walks now and have always been impressed by your professional efficiency.”Revd Moorhouse, 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
“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
“Well organised, good accommodation and places to eat nearby. Good taxi transfers. Stunning scenery. I enjoyed it all for different reasons. Stages 1 & 2 easy walking with good views, stage 3 more challenging but again some great views made it worthwhile.”Dr Bowman, UK
“Loved the contrast of moorland and coast.”Mrs Burrell, 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
“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
“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
“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
Dog friendly