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

“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
“Great walking. Good scenery. Met many friendly people along the way.”
Mr Calvert, UK
“Extremely beautiful walk.”
Dr Hicks, 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
“For most of the walk I just had sheep and Grouse for company. It was isolated and beautiful.”
Mrs Davies, UK
“Stunningly beautiful walk, very enjoyable, would do it again.”
Ms Unwin, UK
“Brilliant holiday in every way.”
Mr Clipson, 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