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.

Customer reviews from the Cleveland Way

“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
“Loved the contrast of moorland and coast.”
Mrs Burrell, 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
“As usual, the staging of the walk and the choice of accommodation were excellent.”
Mr Calderisi, Canada
“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
“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
“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
“I appreciated the efforts made to cut down the daily mileage- my husband managed well and thoroughly enjoyed the holiday.”
Ms Angus, UK
"View to Cleveland Escarpment from near Roseberry Topping" by Bob Parkinson (2019)
"View from Sutton Bank" by Bob Parkinson (2019)
"View from Cringle Moor to Cold Moor" by Bob Parkinson (2019)
"View from Beyond Whitestones" by Bob Parkinson (2019)
"View back to Cringle End" by Bob Parkinson (2019)
"On Holey Moor" by Bob Parkinson (2019)
"Completing the Walk" by Vanessa Burrell (2018 Photo Competition Winner)
"Staithes" by Vanessa Burrell (2018)
"View from Cringle End" by Vanessa Burrell (2018)
"Repus" by Vanessa Burrell (2018)
"Ironwork Scultpure" by Vanessa Burrell (2018)
"Signpost between Whitby and Robin Hoods Bay" by Anne Swindell (2018)
"Heather and Sea near Kettleness" by Carmen Matthews (2018)
"Helmsley Castle" by Carmen Matthews (2018)
"Clifftops near Cloughton" by Carmen Matthews (2018)
"Sheep among Heather" by Carmen Matthews (2018)
"Little Moor" by Carmen Matthews (2018)