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

Cleveland Way 6 nights, 5 days walking

£NNN per person
  • Itinerary
  • What's included?
  • Extra nights?
  • Tour facts
  • Route profile
  • Travel info
  • Weather
  • Holiday Highlights

Important information

Please note that the Filey overnight stop is currently proving difficult to book. If you are looking to book this tour, a transfer to a nearby town, or an upgrade fee to expand the accommodation options available to more expensive properties may be necessary. Please note your preference in the additional info field at the end of the booking form, or contact us directly if you wish to go ahead.

Start

Travel to Helmsley where your first night's accommodation will be booked

Day 1

Helmsley to Osmotherley. 22.5 miles (36km) / 2441 ft (744 m) ascent

Day 2

Osmotherley to Captain Cook's Monument(T). 23 miles (37km) / 3921 ft (1195 m) ascent

Day 3

Captain Cook's Monument(T) to Staithes. 21 miles (34km) / 2822 ft (860 m) ascent

Day 4

Staithes to Robin Hood's Bay. 18.5 miles (29.5km) / 2395 ft (730 m) ascent

Day 5

Robin Hood's Bay to Filey. 25.5 miles (41km) / 3015 ft (919 m) ascent

Finish

Depart from Filey after breakfast

Your Itinerary

This itinerary lists our preferred overnight stops for this tour. Sometimes there may be a shortage of available accommodation in a preferred location, in which case we will transfer you from the trail to your accommodation and back again at no extra charge. Overnight stops marked with a (T) will always require transfers as standard.

Overnight stops marked with an (L) have very limited accommodation, and therefore more often than not will also require a transfer, particularly on bank holidays and weekends. We will use non-transfer accommodation wherever possible.

The daily mileages quoted are average trail miles only and do not include the distance from the trail to your accommodation. We do not expect you to have to travel more than a mile from the trail to your accommodation in most cases; should your accommodation be further than this, transfers will be provided as standard if practical. A very limited number of stops will require you to travel on foot up to two miles off the trail, however these instances will be clearly communicated to you if applicable.

Further transfers may also be required due to some accommodations having a two-night minimum booking policy, especially at weekends.

Below are the additional costs that may apply depending on your requirements. Dog-friendly tours are subject to a Daily Dog Charge, which will be listed below if applicable. Our standard prices per person are based upon two people sharing a room; if you are on your own, or are part of a group but require a room of your own, then the Solo Traveller or Single Supplements apply respectively:

A note about transfers
Solo Traveller Supplement
£70.00 per person / per night
Single Supplement
£55.00 per person / per night


You can add rest days at any of the overnight stops:

Extra night (Standard)
£65.00 per person / per night
Standard
Interactive
© Contours Walking Holidays Cleveland Way map
Helmsley to Filey
111 miles (178 km)
2nd January to 24th December

Holiday highlights

Visiting locations rich in history and heritage, from Rievaulx Abbey, Scarborough Castle and Mount Grace Priory to the inspiration for Dracula in Whitby.

Spotting the variety of wildlife, from grouse in the heather moors to the sea birds along the coastline.

Being rewarded by dramatic coastal views as you reach the North Yorkshire coastline on the approach to Filey.

What's included?

  • 6 nights' accommodation in en-suite rooms (where available) in selected B&B’s, hotels, inns and guesthouses along the trail, or a short distance away via taxi provided at our expense.
  • Breakfast each day.
  • Door to door luggage transfer.
  • Maps with the route marked on and a guidebook or route notes describing the trail.
  • An information pack containing an itinerary, instructions on how to find your accommodation each night and a kit list.
  • Detailed travel instructions on how to get to the start of your holiday and back from the end of it.

Extra Nights & Rest Days

The charming village of Osmotherley, with its neat stone cottages huddled around its green, ancient market cross and stone table where John Wesley preached during one of his sermon tours is a popular choice for an extra night. A lovely short walk from here visits the Lady Chapel and Mount Grace Priory, an attractive 14th century Carthusian monastery.

Staithes is an attractive little fishing village with an interesting exhibition on Captain Cook while another popular choice for an extra night is Robin Hood's Bay, which is within easy reach of Whitby. Here, there is an attractive harbour, atmospheric ruined abbey, Captain Cook Museum, Lifeboat Museum, Whitby Museum and St Mary's Church. The interior of this intriguing church was altered in 1612 to resemble the lower deck of a wooden sailing ship.

You can add rest days at any of the overnight stops:

Extra night (Standard)
£65.00 per person / per night

Tour Facts

Total distance: 111 miles (177.5 km)
Duration: 6 nights, 5 days walking
Minimum daily distance: 18.5 miles (29.5 km)
Maximum daily distance: 25.5 miles (41 km)
Code: CLEVW1 Grade: Strenuous
Season: 2nd January - 24th December
Start of holiday: Helmsley
End of holiday: Filey

Route Profile

Cleveland Way Route Profile

Travel Information

Useful information and travel links that will assist you in your plans to travel to the start of the holiday and back from the end of it are sent to you with your full tour pack. A summary is given below:

By Air - The most convenient major city and international airports are Leeds-Bradford, Manchester and Teesside International Airports.

By Rail - The nearest rail stations to Helmsley are either Malton (about 16.5 miles away) or York (about 25 miles away). There is a rail station at the end of the trail (Filey).

By Bus - There are no direct bus journeys from Malton to Helmsley, so a taxi would be required. There is a rather infrequent bus service from York to Helmsley, Monday to Saturday only, but a taxi would be a much quicker option, and essential on Sundays/in between buses. Various bus services run from Filey.

From London - Trains run from London Kings Cross station to Malton and York. A bus/taxi will be required to Helmsley.

Return To The Start - The easiest way to return to the start of the trail is to take a train from Filey to Malton. From there, a taxi will be required to Helmsley.

Weather Information

To find out more about the weather forecast for your chosen holiday's general location, please see the following websites:

  • MetCheck - This website allows you to look up detailed weather information for specific locations as far as six months in advance.
  • Met Office - This website shows regional area forecasts a few days in advance, with a general UK forecast description of up to 30 days in advance.
  • Mountain Forecast - This website shows what the forecast is like up on specific hills and fells, and offers forecasts a few days in advance.
"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

“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
“Lots of variety with moors and coast. All ran smoothly.”
Mrs Cartledge, UK
“We had read a lot about the Cleveland Way and it met our expectations. There was a nice mix of accommodations.”
Mrs Walker, UK
“9 days of wonderful views and excellent B&Bs. We had a wonderful walk. Met interesting people on the trail and stayed in great places. Thanks to all the team for the perfect organisation. All taxi firms were excellent too.”
Mr Darwen, 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
“Everything was great - the map booklet, luggage transfers, taxis and accommodation. Really enjoyed being out walking all day.”
Mrs Jones, UK
“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
“Really good, it all went very well, organisation was perfect, no complaints! Great scenery, lovely walking, everything went to plan, so we never really thought much about the organisation!”
Mr Astle, UK
Find your holiday