Cleveland Way

A scenic walk from Helmsley to Filey around the edge of the North York Moors National Park.

8 to 11 nights
110 miles
Moderate to Demanding / Strenuous

From £645 per person

Discover the available tours

About this route

This holiday option explores the entirety of the Cleveland Way, 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.

© Contours Walking Holidays Cleveland Way map
Helmsley to Filey
110 miles (176 km)
14th March to 31st October

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.

Available tours

CodeTourDurationDifficultyPrice per person
CLEVW1 From Helmsley to Filey 8 nights, 7 days walking Demanding / Strenuous£645
CLEVW2 From Helmsley to Filey 10 nights, 9 days walking Moderate / Demanding£805
CLEVW3 From Helmsley to Filey 11 nights, 10 days walking Moderate£885

Cleveland Way 8 nights, 7 days walking

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

Travel to Helmsley where your first night's accommodation has been booked

Day 1

Helmsley to Osmotherley. 21.5 miles (34.5km)

Day 2

Osmotherley to Clay Bank Top(T). 11 miles (17.5km)

Day 3

Clay Bank Top(T) to Captain Cook's Monument(T). 11.5 miles (18.5km)

Day 4

Captain Cook's Monument(T) to Staithes. 21 miles (34km)

Day 5

Staithes to Robin Hood's Bay. 18.5 miles (29.5km)

Day 6

Robin Hood's Bay to Scarborough. 14.5 miles (23km)

Day 7

Scarborough to Filey. 12 miles (19km)


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; should your accommodation be further than this, transfers will be provided as standard.

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
£43.00 per person / per night
Single Supplement
£33.00 per person / per night

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

Extra night (Standard)
£60.00 per person / per night

What's included?

  • 8 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.

If you fancy somewhere livelier, consider the bustling resort of Scarborough.

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

Extra night (Standard)
£60.00 per person / per night

Tour Facts

Total distance: 110 miles (176 km)
Duration: 8 nights, 7 days walking
Minimum daily distance: 11 miles (17.5 km)
Maximum daily distance: 21.5 miles (34.5 km)
Code: CLEVW1 Grade: Demanding / Strenuous
Season: 14th March - 31st October
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 Durham Tees Valley.

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 - Various bus services run to Helmsley and from Filey.

From London - Trains run from London Kings Cross station to Malton. From there 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 bus/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.

Routes on this trail

6 nights
57 miles
From £510 per person
A walking holiday from Helmsley to Saltburn-by-the-Sea through the green dales of the North York Moors.Find Out More
5 to 6 nights
54 miles
Dog friendly
From £425 per person
A self-guided walk along the stunning Cleveland Heritage Coast from Saltburn-by-the Sea to Filey.Find Out More
3 nights
22 miles
From £255 per person
A short, pleasant walk along the Cleveland Way National Trail from Helmsley to Osmotherley.Find Out More

Customer reviews from the Cleveland Way

“Brilliant holiday in every way.”
Mr Clipson, UK
“As usual, the staging of the walk and the choice of accommodation were excellent.”
Mr Calderisi, Canada
“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
“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
“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
“The combination of the moors and the sea coast is stunningly beautiful and provides great variety in the terrain and views. I am amazed at the amount of work that has gone into creating and maintaining the trail. This was my fourth holiday with Contours; I expect to book more in the future.”
Ms Matthews, USA
“The variety of landscapes on the Cleveland Way was really nice. The luggage transportation was flawless and the variety of lodging hosts and facilities was terrific. Well done!”
Mr McCoy, USA
"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)

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