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 £402 per person

Find your holiday

About the trail

Art of Richard Farrington's Giant Charm Bracelet, found on the Cleveland Way.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 £798 per person

Cleveland Way

The Cleveland Way spans 111 miles, from Helmsley to Filey. This self-guided walking holiday 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 £798
CLEVW2 From Helmsley to Filey 8 nights, 7 days walking Demanding / Strenuous £1056
CLEVW3 From Helmsley to Filey 10 nights, 9 days walking Moderate / Demanding £1308
CLEVW4 From Helmsley to Filey 11 nights, 10 days walking Moderate £1434

Short breaks

Code Tour Duration Difficulty Price per person
CLEVWSB From Helmsley to Osmotherley 3 nights, 2 days walking Moderate £402
"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

“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
“Four days good walking, with rain on one day only! Overall excellent. The Cleveland Way is an excellent walk. It can be demanding and the geography means accommodation can be widely spaced, making for some long sections. I've walked with Contours on five long distance walks now and have always been impressed by your professional efficiency.”
Revd Moorhouse, UK
“Everything went to plan, even the weather!”
Mr Newton, UK
“I was lucky with the weather. I had only one day with rain and two days with some drizzle. The views were great. And I met interesting people. The Cleveland Way is an excellent mixture of moorland and coastal walk with some places of history, e.g. Rievaulx Abbey, Whitby Abbey. Again the team of Contours did a good job. It was my walk no 14 with Contours!”
Mr Witzel, Germany
“Extremely beautiful walk.”
Dr Hicks, UK
“The weather was very good apart from the last morning which made the whole walk stunning.”
Mrs Edwards, UK
“Brilliant holiday in every way.”
Mr Clipson, UK
“A well organised holiday walking a lovely route.”
Mr Whiley, UK
“Just a quick note that our Cleveland Way walk booked through Contours was absolutely great, assisted by some great weather it must be said.”
Mr Flather, UK
Find your holiday