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 £390 per person

Find your holiday

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.

Choose your route

  • This route includes dog friendly tour options Cleveland Way
  • This route includes dog friendly tour options Cleveland Way - Moors Section
  • This route includes dog friendly tour options Cleveland Way - Coast Section
  • This route includes dog friendly tour options Cleveland Way Short Break

Dog friendly tours available

Dogs are welcome on select routes along this trail. Look for the pawprint icon when choosing your holiday.

Trail running tours available

We also organise trail running holidays along this route. Find out more.

About this route

6 to 11 nights
111 miles
Moderate to Strenuous
2nd January to 24th December
Includes Dog-Friendly Tours

From £760 per person

Cleveland Way

Book your self-guided walking holiday along the Cleveland Way. This holiday option explores the entirety of the National Trail, from the tranquil beauty of the North York Moors National Park to the bustling fishing ports of the Cleveland Heritage Coast.

There is plenty of spectacular scenery and amazing history to discover along this 110-mile walking trail, with something new to take in at every turn. As the landscape changes from heather-clad moors and green dales to sandy beaches and breezy clifftops, the walk visits a range of old market towns and fishing villages, each boasting their own unique character and warm welcome.

Available tours

Code Tour Duration Difficulty Price per person
CLEVW1 From Helmsley to Filey 6 nights, 5 days walking Strenuous £760
CLEVW2 From Helmsley to Filey 8 nights, 7 days walking Demanding / Strenuous £1005
CLEVW3 From Helmsley to Filey 10 nights, 9 days walking Moderate / Demanding £1245
CLEVW4 From Helmsley to Filey 11 nights, 10 days walking Moderate £1365

Short breaks

Code Tour Duration Difficulty Price per person
CLEVWSB From Helmsley to Osmotherley 3 nights, 2 days walking Moderate £390
"Saltburn Viaduct" by Raul Susmel (2024) "Saltburn Viaduct" by Raul Susmel (2024)
"View Towards Skinningrove" by Annabel Grant (2023) "View Towards Skinningrove" by Annabel Grant (2023)
"Cliffs between Saltburn and Staithes" by Annabel Grant (2023) "Cliffs between Saltburn and Staithes" by Annabel Grant (2023)
"Resting at Boulby Mine Bench" by Annabel Grant (2023) "Resting at Boulby Mine Bench" by Annabel Grant (2023)
"Scarborough South Bay" by Annabel Grant (2023) "Scarborough South Bay" by Annabel Grant (2023)
"View from Filey Brigg" by Annabel Grant (2023) "View from Filey Brigg" by Annabel Grant (2023)
"Saltburn from its Pier" by Neil Flather (2023) "Saltburn from its Pier" by Neil Flather (2023)
"Farewell to Runswick Bay" by Neil Flather (2023) "Farewell to Runswick Bay" by Neil Flather (2023)
"Above Ingleby Incline looking back to Clay Bank" by Neil Flather (2023) "Above Ingleby Incline looking back to Clay Bank" by Neil Flather (2023)
"Cringle Moor" by Raymond Riggs (2023) "Cringle Moor" by Raymond Riggs (2023)
"Signpost at Scarth Nick" by Raymond Riggs (2023) "Signpost at Scarth Nick" by Raymond Riggs (2023)
"Cake at Lord Stones Cafe" by Raymond Riggs (2023) "Cake at Lord Stones Cafe" by Raymond Riggs (2023)
"Forest Near Hambleton" by Raymond Riggs (2023) "Forest Near Hambleton" by Raymond Riggs (2023)
"Kepwick Moor" by Raymond Riggs (2023) "Kepwick Moor" by Raymond Riggs (2023)
"Grouse at Little Moor" by Raymond Riggs (2023) "Grouse at Little Moor" by Raymond Riggs (2023)
"Saltburn" by Bridget Casson (2021) "Saltburn" by Bridget Casson (2021)
"Ring Sculpture" by Bridget Casson (2021) "Ring Sculpture" by Bridget Casson (2021)
"On the Beach at Sandsend" by Bridget Casson (2021) "On the Beach at Sandsend" by Bridget Casson (2021)
"Between Saltburn and Staithes" by Bridget Casson (2021) "Between Saltburn and Staithes" by Bridget Casson (2021)
"Saltburn-by-the-Sea" by Thomas Witzel (2019) "Saltburn-by-the-Sea" by Thomas Witzel (2019)
"Staithes" by Thomas Witzel (2019) "Staithes" by Thomas Witzel (2019)
"View from Urra Moor" by Thomas Witzel (2019) "View from Urra Moor" by Thomas Witzel (2019)
"Scarborough" by Thomas Witzel (2019) "Scarborough" by Thomas Witzel (2019)
"View to Cleveland Escarpment from near Roseberry Topping" by Bob Parkinson (2019) "View to Cleveland Escarpment from near Roseberry Topping" by Bob Parkinson (2019)
"View from Sutton Bank" 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 Cringle Moor to Cold Moor" by Bob Parkinson (2019)
"View from Beyond Whitestones" by Bob Parkinson (2019) "View from Beyond Whitestones" by Bob Parkinson (2019)
"View back to Cringle End" by Bob Parkinson (2019) "View back to Cringle End" by Bob Parkinson (2019)
"On Holey Moor" by Bob Parkinson (2019) "On Holey Moor" by Bob Parkinson (2019)
"Completing the Walk" by Vanessa Burrell (2018 Photo Competition Winner) "Completing the Walk" by Vanessa Burrell (2018 Photo Competition Winner)
"Staithes" by Vanessa Burrell (2018) "Staithes" by Vanessa Burrell (2018)
"View from Cringle End" by Vanessa Burrell (2018) "View from Cringle End" by Vanessa Burrell (2018)
"Repus" by Vanessa Burrell (2018) "Repus" by Vanessa Burrell (2018)
"Ironwork Scultpure" by Vanessa Burrell (2018) "Ironwork Scultpure" by Vanessa Burrell (2018)
"Signpost between Whitby and Robin Hoods Bay" by Anne Swindell (2018) "Signpost between Whitby and Robin Hoods Bay" by Anne Swindell (2018)
"Heather and Sea near Kettleness" by Carmen Matthews (2018) "Heather and Sea near Kettleness" by Carmen Matthews (2018)
"Helmsley Castle" by Carmen Matthews (2018) "Helmsley Castle" by Carmen Matthews (2018)
"Clifftops near Cloughton" by Carmen Matthews (2018) "Clifftops near Cloughton" by Carmen Matthews (2018)
"Sheep among Heather" by Carmen Matthews (2018) "Sheep among Heather" by Carmen Matthews (2018)
"Little Moor" by Carmen Matthews (2018) "Little Moor" by Carmen Matthews (2018)
"Roseberry Topping" by Stuart Inglis (2017) "Roseberry Topping" by Stuart Inglis (2017)
"Mount Grace Priory" by Stuart Inglis (2017) "Mount Grace Priory" by Stuart Inglis (2017)
"Hang-gliding on Easby Moor" by Stuart Inglis (2017) "Hang-gliding on Easby Moor" by Stuart Inglis (2017)
"Guisborough Priory" by Stuart Inglis (2017) "Guisborough Priory" by Stuart Inglis (2017)
"Staithes" by Stuart Inglis (2017) "Staithes" by Stuart Inglis (2017)
"View across Robin Hoods Bay" by Bob Parkinson (2017) "View across Robin Hoods Bay" by Bob Parkinson (2017)
"View of Runswick Bay" by Bob Parkinson (2017) "View of Runswick Bay" by Bob Parkinson (2017)
"Approaching Ravenscar" by Bob Parkinson (2017) "Approaching Ravenscar" by Bob Parkinson (2017)
"View over Whitby" by Bob Parkinson (2017) "View over Whitby" by Bob Parkinson (2017)
"Whitby Abbey" by Bob Parkinson (2017) "Whitby Abbey" by Bob Parkinson (2017)
"Descent from Roseberry Topping" by Christine Harrison (2016) "Descent from Roseberry Topping" by Christine Harrison (2016)
"Kettle Ness from Runswick Bay" by Pauline Ellington (2016) "Kettle Ness from Runswick Bay" by Pauline Ellington (2016)
"Roseberry Topping" by Pat Fergusson (2016) "Roseberry Topping" by Pat Fergusson (2016)
"Saltburn-by-the-sea to Staithes" by Pat Fergusson (2016) "Saltburn-by-the-sea to Staithes" by Pat Fergusson (2016)
"Scalby Mill" by Christine Harrison (2016) "Scalby Mill" by Christine Harrison (2016)
"Staithes" by Christine Harrison (2016) "Staithes" by Christine Harrison (2016)

Customer reviews from the Cleveland Way

“All the Contours organised bits went very smoothly. Exceptional weather too.”
Mr Nield, UK
“Excellent choice of stays.”
Mr Hallatt, UK
“Everything was great - the map booklet, luggage transfers, taxis and accommodation. Really enjoyed being out walking all day.”
Mrs Jones, UK
“Loved the contrast of moorland and coast.”
Mrs Burrell, UK
“Lots of variety with moors and coast. All ran smoothly.”
Mrs Cartledge, 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
“Everything went to plan, even the weather!”
Mr Newton, 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
“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
Find your holiday