Cleveland Way

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

3 to 11 nights
22-110 miles
Moderate to Demanding / Strenuous

From £250 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
110 miles
Moderate+
Dog friendly
From £630 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 £495 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 £415 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 £250 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

“As usual, the staging of the walk and the choice of accommodation were excellent.”
Mr Calderisi, Canada
“Loved the contrast of moorland and coast.”
Mrs Burrell, 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
“Extremely beautiful walk.”
Dr Hicks, UK
“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
“Brilliant holiday in every way.”
Mr Clipson, 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
“Great walking. Good scenery. Met many friendly people along the way.”
Mr Calvert, 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