Cleveland Way
A scenic walk from Helmsley to Filey around the edge of the North York Moors National Park.
6 to 11 nights
111 miles
Moderate to Strenuous
From £525 per person
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 scenic walk from Helmsley to Filey around the edge of the North York Moors National Park.
From £525 per person
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.
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.
| Code | Tour | Duration | Price per person | |
|---|---|---|---|---|
| CLEVW1 | From Helmsley to Filey | 5 days walking | £525 | |
| CLEVW2 | From Helmsley to Filey | 7 days walking | £695 | |
| CLEVW3 | From Helmsley to Filey | 9 days walking | £865 | |
| CLEVW4 | From Helmsley to Filey | 10 days walking | £950 |
Travel to Helmsley where your first night's accommodation has been 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; 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:
You can add rest days at any of the overnight stops:
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:
“Extremely beautiful walk.”Dr Hicks, UK
“Thanks for the excellent arrangements. Wonderful walk - lucky with weather - no rain! Hope to be fit enough for another trail!”Mrs Gambier, 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
“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
“As usual, the staging of the walk and the choice of accommodation were excellent.”Mr Calderisi, Canada
“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
“Excellent accommodation and the bag transfer worked well.”Mr Horobin, UK
“Brilliant holiday in every way.”Mr Clipson, 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
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Dog friendly