Cleveland Way
106 fantastic miles of mixed coastal and moorland walking

The Cleveland Way is a long distance National Trail of 106 miles in length, commencing in the town of Helmsley, and finishing in Filey.

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Holiday Packages

All our Standard Itineraries include:

  • Hand-picked accommodation in B&Bs / guest houses / inns / small hotels
  • En-suite facilities where available
  • Breakfast
  • Daily baggage transfers from our own team of local drivers
  • All booking fees

We will also endeavour to include all these in any custom itinerary you wish to build for this walk.

Day 1: Helmsley to Kilburn (9.8m)
Day 2: Kilburn to Osmotherley (13.9m)
Day 3: Osmotherley to Clay Bank Top (10.8m)
Day 4: Clay Bank Top to Great Ayton (13.3m)
Day 5: Great Ayton to Saltburn (14.7m)
Day 6: Saltburn to Staithes (8.4m)
Day 7: Staithes to Whitby (10.8m)
Day 8: Whitby to Ravenscar (10.4m)
Day 9: Ravenscar to Scarborough (North) (10.2m)
Day 10: Scarborough to Filey (10.2m)

 

£825 per person (based on two sharing)

 

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Day 1: Helmsley to Osmotherley (19.1m)
Day 2: Osmotherley to Great Ayton (24.2m)
Day 3: Great Ayton to Staithes (23.7m)
Day 4: Staithes to Robin Hoods Bay (18.2m)
Day 5: Robin Hoods Bay to Filey Brigg (23.6m) or town (24.7m)

 

£505 per person (based on two sharing)

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Day 1: Helmsley to High Paradise (14.4m)
Day 2: High Paradise to Clay Bank Top (17.9m)
Day 3: Clay Bank Top to Slapewath (19.3m)
Day 4: Slapewath to Runswick Bay (15.8m)
Day 5: Runswick Bay to Ravenscar (18.3m)
Day 6: Ravenscar to Filey Brigg (19.3m) or town (20.4m)

 

£585 per person (based on two sharing)

 

Get a Personal Quote

Day 1: Helmsley to High Paradise (14.4m)
Day 2: High Paradise to Clay Bank Top (17.9m)
Day 3: Clay Bank Top to Newton under Roseberry (14.3m)
Day 4: Newton under Roseberry to Skinningrove (14.9m)
Day 5: Skinningrove to Whitby (15.5m)
Day 6: Whitby to Cloughton (16.5m)
Day 7: Cloughton to Filey Brigg (14.8m) or town (15.9m)

 

£620 per person (based on two sharing)

 

Get a Personal Quote

Day 1: Helmsley to High Paradise (14.4m)
Day 2: High Paradise to Clay Bank Top (17.9m)
Day 3: Clay Bank Top to Newton under Roseberry (14.3m)
Day 4: Newton under Roseberry to Saltburn (10.9m)
Day 5: Saltburn to Runswick Bay (11.3m)
Day 6: Runswick Bay to Robin Hoods Bay (14.8m)
Day 7: Robin Hoods Bay to Scarborough (North) (13.7m)
Day 8: Scarborough to Filey Brigg (10.2m) or town (11.3m)

 

£680 per person (based on two sharing)

 

Get a Personal Quote

Day 1: Helmsley to High Paradise (14.4m)
Day 2: High Paradise to Ingleby Cross (8.9m)
Day 3: Ingleby Cross to Clay Bank Top (10.4m)
Day 4: Clay Bank Top to Great Ayton (13.7m)
Day 5: Great Ayton to Saltburn (13.9m)
Day 6: Saltburn to Runswick Bay (11.3m)
Day 7: Runswick Bay to Robin Hoods Bay (11.3m)
Day 8: Robin Hoods Bay to Scarborough (North) (13.7m)
Day 9: Scarborough to Filey Brigg (10.2m) or town (11.3m)

 

£760 per person (based on two sharing)

 

Get a Personal Quote

Day 1: Helmsley to Kilburn (9.8m)
Day 2: Kilburn to Osmotherley (13.9m)
Day 3: Osmotherley to Clay Bank Top (10.8m)
Day 4: Clay Bank Top to Kildale (9.8m)
Day 5: Kildale to Slapewath (10.5m)
Day 6: Slapewath to Skinningrove (8.2m)
Day 7: Skinningrove to Runswick Bay (7.7m)
Day 8: Runswick Bay to Whitby (7.9m)
Day 9: Whitby to Ravenscar (10.4m)
Day 10: Ravenscar to Scarborough (North) (10.2m)
Day 11: Scarborough to Filey Brigg (10.2m) or town (11.3m)

 

£900 per person (based on two sharing)

 

Get a Personal Quote

Day 1: Helmsley to High Paradise (14.4m)
Day 2: High Paradise to Ingleby Cross (8.9m)
Day 3: Ingleby Cross to Clay Bank Top (10.4m)
Day 4: Clay Bank Top to Great Ayton (13.7m)
Day 5: Great Ayton to Saltburn (13.9m)

 

£465 per person (based on two sharing)

 

Get a Personal Quote

Day 1: Saltburn to Staithes (8.4m)
Day 2: Staithes to Whitby (10.8m)
Day 3: Whitby to Ravenscar (10.4m)
Day 4: Ravenscar to Scarborough (North) (10.2m)
Day 5: Scarborough to Filey Brigg (10.2m) or town (11.3m)

 

£455 per person (based on two sharing)

 

Get a Personal Quote

* All headline holiday prices are shown per person, based on two people sharing.

Baggage Transfer

Baggage Transfer is automatically included in the price of all our Walking Holiday packages.

These prices are for anyone planning their own holiday and just need bags moving from one stop to the next.

£12.00 per person per day (minimum of two persons)
£8.50 per person per day
(minimum of four persons)

 

Max 17kg per bag

£17.00 per person per day (minimum of two persons)
£9.00 per person per day
(minimum of four persons)

 

Max 17kg per bag

£15.00 per person per day (minimum of two persons)
£8.50 per person per day
(minimum of four persons)

 

Max 17kg per bag

£14.00 per person per day (minimum of two persons)
£8.50 per person per day
(minimum of four persons)

 

Max 17kg per bag

Note: If you are booking accommodation in an Airbnb, you must ensure that there will either be someone available to take collection/delivery of your bags or that they have appropriate, secure storage in the event that the proprietor is absent.

Walk Information

  • Holiday Options
  • Walk Info
  • Maps & Guide Books

Rest Days
Rest days can be incorporated into any walking holiday package at an additional £50.00 per person per night

Solo Travellers
Solo travellers please contact us or use the booking form to send your proposed itinerary including dates, and we will price accordingly. Where possible, we take advantage of existing bookings from other clients to ensure you receive a cost effective service.

Alternative Itineraries
For alternative itineraries to those provided for this route, please contact us, or use the Booking Form to submit your proposed itinerary and number of participants and we will quote accordingly.

Walking Season Dates
Prices are based on the walk starting after 1st April and ending before 30th September. For walks outside those dates, please contact us. We provide a reduced out of season service, but still manage to meet the needs of most customers who contact us during this period.

Walk Information

The Cleveland Way is a long distance National Trail of 110 miles in length, commencing in the town of Helmsley, and finishing in Filey, on the North Sea coast, having traversed in an arc around the North York Moors to the sea at Saltburn, and then southwards along the coastal path. It is unique among British Trails, in that the walk passes through inland scenery which includes wild heather moorland, limestone escarpments and river valleys, arable farmland, and wooded country. Clifftop walking, with spectacular views of the sea, constitutes the majority of the second half of the journey from Saltburn to Filey, affording observation at close quarters of very many species of sea birds, to interest the ornithologist, whilst in many locations, sheltered wooded ravines running inland contain rich flora and fauna, to interest the naturalist.

Most walkers of average ability take between 8 and 10 days to complete the trail, averaging about 12 miles per day, but subject to availability of accommodation, daily distances can be adjusted to suit the walkers requirements. However, as in all upland regions of Britain, it is important to be prepared for the wide range of weather conditions which can be experienced, particularly the chilly winds and sea frets which blow from the North Sea. Paths and tracks on the moors are predominantly stony, but along the coastal path the going can be very slippery, and care must be taken on this section where in places, sections of high cliffs are occasionally prone to erosion and land-slips. Although some steep slopes are encountered on the Cleveland Way, gradients and ground conditions are unlikely to present the same degree of danger as true mountain country.

As with the other walks we cover, apart from our door to door baggage courier service, we can arrange your accommodation on a Bed & Breakfast basis (we arrange accommodation where evening meals are available locally) at local inns, hotels, or guest houses, and you will be assured of a pleasant burden-free walk, with warm, dry clothing and other creature comforts ready for you at the end of each day.

OS Explorer Maps
OL26 - North York Moors - Western area
OL27 - North York Moors - Eastern area

Other Maps
"Cleveland Way A-Z Adventure Atlas" - Published by Geographers’ A-Z Maps - ISBN: 978-1-78257-196-4

Guide Books
"The Cleveland Way and the Yorkshire Wolds Way (British Long Distance)" by Paddy Dillon - Published by Cicerone

ViewRanger Digital Maps
Digital Maps can be viewed on a modern smartphone using an appropriate ‘app’, which is usually provided as part of any map purchase. Brigantes are happy to recommend ViewRanger for all your digital mapping and mobile navigation needs.

The ViewRanger Shop provides Ordnance Survey maps for all parts of the UK, as well as the National Trail and selected Long Distance Paths. Map segments can also be purchased ad-hoc, allowing you to cover any walk you plan to take.

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Walkers' Testimonials

Have you walked this route? Please leave a review and let others know what you think.

Use the comments form below to submit your testimonial for this walk. Rest assured, we won’t display or disclose your email address! It is only required to prevent spam – and to enable you to receive notifications of any responses to your review should you select the option to do so.

15 Replies to “Cleveland Way”

  1. Thanks to Brigantes for arranging the accommodation and transport for our walk along the Cleveland Way. 110 miles in 7 days was a challenge for a 70 and 69 year old, but we could relax and concentrate on our walking in the knowledge that the logistics would be spot on. We have used Brigantes before and, God willing, will do so again.

  2. Four of us (total age 262, well oiled walking machines) walked the Cleveland way this month. Booked it through Brigantes, whose organisation was faultless – all accommodation was fine, hosts were very personable, all baggage transfers completely efficient. Will certainly be happy to book further walks through Brigantes.

  3. Despite walking ‘the wrong way,’ as everyone we met kept telling us, ie. heading north from Whitby, Brigantes gave an excellent service from my first enquiry to our last days walking. (We met a lot of other walkers by going this way round) The luggage transfers were magical, the route well marked and our accommodation varied and interesting with some delightful hosts.

  4. Another very successful trip organised by Brigantes (last year I did the Pennine Journey). All the organisation ran extremely smoothly – B&Bs ranged from perfectly satisfactory to excellent and my bag was always waiting for me. The path is very clearly marked and the scenery spectacular. Would certainly recommend both the walk and Brigantes.

  5. Used Brigantes for the second time, and very much last minute, doing the Cleveland Way, and also the Tabular Hills Walk to get back to Helmsley, which other companies would not include, and they were brilliant.Everything went according to plan, with the few tiny hiccups quickly sorted out. We will certainly use them again in future … as long as our elderly legs keep walking!

  6. We finished the Cleveland Way from Runswick Bay to Filey,adding a leg from Filey to Bridlington. Used Brigantes for baggage transfer for the third time and as before, everything went very well. We now intend to use this service every year.

  7. Once again we used Brigantes after the success of our previous walk doing the first half of the Cleveland Way, and once again Brigantes came up trumps transporting our bags down the coast from Saltburn to Scarborough. All our party of seven very well educated, though ageing walkers, had nothing but praise for Brigantes. Once again, we left our bags in reception at host hotel, and once again they were magically teleported to our destination, ready for our arrival. An excellent service throughout, from booking, communication and delivery. A beautiful walk from Saltburn to Scarborough aided and enhanced by great back up service, many many thanks. Trevor and chaps, May 2017.

  8. Mother and Son Walking the Cleveland way in August 2016 (We’ve just come back) I can only agree with Trevor Thomas. We do thank Brigantes for having done such an excellent job. Having worked in tourism myself, I am quite much aware of all the odds that can happen! We had none! Accomodation and baggage Transfers worked out perfectly.
    Thanks again and a big “hello'” from Hamburg.

  9. Seven educated gentlemen walked the Cleveland Way between Sutton Bank and Saltburn, Apr-May 2016. We used Brigantes as our luggage transfer carriers and they were simply “Brilliant” in every respect. The communication whilst booking was superb, the detail provided was excellent, and the job itself was executed very very professionally. So much so, we never saw a driver, we simply left our bags in reception at our host hotel, to be ‘teleported’ to our destination, and were ready when we arrived. No idea how it happened, but it just did!!

    Great job, will be definitely using Brigantes again

  10. We loved the walk you helped us plan and walk. Everybody we met has been so enthusiastic about their bit of the country and the walk in particular. You have some good hosts. One of Anne’s favourites was Glenda Calvert at Pry House Farm, Keld.

  11. Just to let you know that we thoroughly enjoyed our C2C this year (Ingleby Cross to Glaisdale). Many thanks for all your excellent arrangements on our behalf. We would highly recommend Park House and also Blakey Ridge. We’ll be back next year for the final stage.

  12. We thought that you might like to know that we successfully completed the C2C, arriving home last Saturday, fit and well without one blister between us. We’d like to thank Brigantes for the wonderful service we received from you.Undertaking the C2C was an absolutely wonderful experience and we enjoyed every minute of it (well, maybe not finding ourselves a few miles along High Street instead of at Kidsty Pike – luckily our only route finding mistake) and would recommend it to anyone wanting a challenge – especially if they have their main luggage carried by a reliable company.

  13. Just a quick thank you for the wonderful job you all did moving our bags. I can’t imagine at my advanced age carrying all of my gear again, so it’s a miracle to have a service like yours. We highly recommend Brigantes to everyone we meet, including your other services (we met a group using the camping accommodations…brilliant!).

  14. I have been meaning to email you and thank you for our holiday back in May. Jane and I had a fabulous time and all our drivers and accommodation were fab. Thank you to Brigantes for such a memorable time.

  15. Our praying didn’t help much as we had rain most days, but it was a wonderful experience. Thanks for all your organizing, especially as it was last minute, and thanks from Lori for the rides in the baggage train! We enjoyed the second half (mostly in Yorkshire) more, as the people and the environment were more real and down to earth (the Lake District was more commercial) Every evening we had wonderful experiences in B&B’s and pubs, the people, the food and the interesting brews.

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