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 £240 per person

Cleveland Way

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.