Cleveland Way

A self-guided walk around the North York Moors National Park and the Cleveland Heritage Coast.

3 to 11 nights
22-111 miles
Moderate to Demanding / Strenuous

From £245 per person

About The Trail

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 walk the entire trail, simply select the first option from the list below.

Dog friendly tours available

Dogs are welcome on select routes along this trail. Look for the pawprint icon when choosing your holiday.

Trail running available

We also organise trail running holidays along this trail. Visit Contours Trail Running Holidays.

Customer reviews from the Cleveland Way

“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
“One of the best holidays we have had. Accommodation, owners, directions and locations all perfect. Many thanks. We will be using Contours again.”
Mr Pickup, UK
“Easy cliff top walking along the beautiful Yorkshire Coast, blessed by glorious weather. Very well signposted throughout. One of our best Contours walks to date.”
Mr Parkinson, UK
“I found the walk very interesting particularly the views across to the Pennines. I found the selection of B&B's very good and would certainly recommend your company to others.~”
Mr Wood, UK
“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
“For most of the walk I just had sheep and Grouse for company. It was isolated and beautiful.”
Mrs Davies, UK
“A lovely coastal walk with accommodation and luggage transfer well organised.”
Mr Pearson, UK
“I appreciated the efforts made to cut down the daily mileage- my husband managed well and thoroughly enjoyed the holiday.”
Ms Angus, UK
“A brilliant walk arranged by yourselves of course and helped by perfect walking weather, all the accommodations were good. Once again thanks for a great holiday and let us know when we need to book for next April.”
Mr Bottomley, UK