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Cleveland Way

Cleveland Way

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

3 to 11 nights
23-111 miles
Moderate to Strenuous

From £290 per person

About the trail

Take a self-guided walking holiday along the Cleveland Way, a walk of stunning contrasts. 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 experience 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.

Customer reviews from the Cleveland Way

“Wonderful scenery, great variety of terrain, interesting towns and villages on the way. Accommodation varied but overall good.”
Mrs Wood, UK
“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
“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
“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
“Excellent accommodation and the bag transfer worked well.”
Mr Horobin, 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
“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
“A lovely coastal walk with accommodation and luggage transfer well organised.”
Mr Pearson, UK
“I appreciated the efforts made to cut down the daily mileage- my husband managed well and thoroughly enjoyed the holiday.”
Ms Angus, UK
"Saltburn-by-the-Sea" by Thomas Witzel (2019)
"Staithes" by Thomas Witzel (2019)
"View from Urra Moor" by Thomas Witzel (2019)
"Scarborough" by Thomas Witzel (2019)
"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)
"Roseberry Topping" by Stuart Inglis (2017)
"Mount Grace Priory" by Stuart Inglis (2017)
"Hang-gliding on Easby Moor" by Stuart Inglis (2017)
"Guisborough Priory" by Stuart Inglis (2017)
"Staithes" by Stuart Inglis (2017)
"View across Robin Hoods Bay" by Bob Parkinson (2017)
"View of Runswick Bay" by Bob Parkinson (2017)
"Approaching Ravenscar" by Bob Parkinson (2017)
"View over Whitby" by Bob Parkinson (2017)
"Whitby Abbey" by Bob Parkinson (2017)
"Descent from Roseberry Topping" by Christine Harrison (2016)
"Kettle Ness from Runswick Bay" by Pauline Ellington (2016)
"Roseberry Topping" by Pat Fergusson (2016)
"Saltburn-by-the-sea to Staithes" by Pat Fergusson (2016)
"Scalby Mill" by Christine Harrison (2016)
"Staithes" by Christine Harrison (2016)