Cleveland Way
Self-guided walking holidays along the Cleveland Way. Accommodation, luggage transfer and custom holiday pack included.
Cleveland Way
https://www.contours.co.uk/cleveland-way
A self-guided walk around the North York Moors National Park and the Cleveland Heritage Coast.
From £380 per person
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.
Dogs are welcome on select routes along this trail. Look for the pawprint icon when choosing your holiday.
We also organise trail running holidays along this route. Find out more.
From £725 per person
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.
| Code | Tour | Duration | Price per person | |
|---|---|---|---|---|
| CLEVW1 | From Helmsley to Filey | 5 days walking | £725 | |
| CLEVW2 | From Helmsley to Filey | 7 days walking | £955 | |
| CLEVW3 | From Helmsley to Filey | 9 days walking | £1185 | |
| CLEVW4 | From Helmsley to Filey | 10 days walking | £1305 |
| Code | Tour | Duration | Price per person | |
|---|---|---|---|---|
| CLEVWSB | From Helmsley to Osmotherley | 2 days walking | £380 |
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.
Travel to Helmsley where your first night's accommodation will be booked
Helmsley to Osmotherley. 22.5 miles (36km) / 2441 ft (744 m) ascent
Osmotherley to Captain Cook's Monument(T). 23 miles (37km) / 3921 ft (1195 m) ascent
Captain Cook's Monument(T) to Staithes. 21 miles (34km) / 2822 ft (860 m) ascent
Staithes to Robin Hood's Bay. 18.5 miles (29.5km) / 2395 ft (730 m) ascent
Robin Hood's Bay to Filey. 25.5 miles (41km) / 3015 ft (919 m) ascent
Depart from Filey after breakfast
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:
You can add rest days at any of the overnight stops:
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.
You can add rest days at any of the overnight stops:
To find out more about the weather forecast for your chosen holiday's general location, please see the following websites:
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“The best hiking trail we have done, very lucky with the weather, but some excellent hiking, a good mix of easy hiking and harder section. Visited some very nice towns, and excellent moorland and coastal hiking. Great hiking, superb scenery, some very good meals out, some very good accommodation. Will absolutely book with you again, this was our 5th, I think, and best.”Miss Steggall, UK
“Lots of variety with moors and coast. All ran smoothly.”Mrs Cartledge, UK
“All the Contours organised bits went very smoothly. Exceptional weather too.”Mr Nield, UK
“Excellent accommodation and the bag transfer worked well.”Mr Horobin, UK
“Everything went to plan, even the weather!”Mr Newton, UK
“Thanks for the excellent arrangements. Wonderful walk - lucky with weather - no rain! Hope to be fit enough for another trail!”Mrs Gambier, UK
“A well organised holiday walking a lovely route.”Mr Whiley, UK
“Yes this was a great walk which I really enjoyed particularly the contrast between the moorland of the first few days and the coast thereafter. I really enjoyed it all and would do it all again although I might book an additional day in Scarborough next time to see round the town more. I think this holiday has something for everyone whatever type of walker you are.”Mr Madge, UK
“Brilliant holiday in every way.”Mr Clipson, UK
Dog friendly