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.

Routes on this trail

Cleveland Way

8 to 11 nights
111 miles
Moderate+
Dog friendly
From £605 per person
A scenic walk from Helmsley to Filey around the edge of the North York Moors National Park.Find Out More

Cleveland Way - Moors Section

6 nights
57 miles
Moderate
From £485 per person
A walking holiday from Helmsley to Saltburn-by-the-Sea through the green dales of the North York Moors.Find Out More

Cleveland Way - Coast Section

5 to 6 nights
54 miles
Moderate+
Dog friendly
From £405 per person
A self-guided walk along the stunning Cleveland Heritage Coast from Saltburn-by-the Sea to Filey.Find Out More

Cleveland Way Short Break

3 nights
22 miles
Moderate
From £245 per person
A short, pleasant walk along the Cleveland Way National Trail from Helmsley to Osmotherley.Find Out More

Customer reviews from the Cleveland Way

“Loved the contrast of moorland and coast.”
Mrs Burrell, 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
“A lovely coastal walk with accommodation and luggage transfer well organised.”
Mr Pearson, 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
“Great walking. Good scenery. Met many friendly people along the way.”
Mr Calvert, 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
“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
“This was the best long distance trail to date that I have had the pleasure of walking. The scenery was amazing – countryside, moorland and coast all in one package. Challenging in places but doable.”
Mr Wilson, UK