The Cleveland Way offers a varied journey through the North York Moors National Park and the Cleveland Heritage Coast, following a well structured, multifarious route that stands to be one of the best walking experiences in England.
Highlights
Start you walk with historic path from Helmsley Castle to Rievaulx Abbey
Spectacular views from Sutton Bank over the Vale of Mowbray
End your walk at the coast, with the Victorian seaside towns of Whitby, Scarborough and Filey
Roseberry Topping, a prominent feature of the landscape and a great vantage point for views over the moors
Robin Hood Bay, Staithes and Runswick Bay - picturesque fishing villages tucked away along the coast
Cliff top walks with incredible views over the Tees lowlands and Bilsdale valley
Your walking holiday begins at the attractive market town of Helmsley, in the heart of the North York Moors National Park. Around 80 percent of the Cleveland Way lies within the National Park, the largest area of moorland in England before reaching the North Sea coast.
The way-marked path climbs the remote upland moors, culminating at the highest point-Urra Moor. From here, you can take stock and reflect on how far you've come, and gazing out into the expansive Yorkshire landscape - it's hard not to take pride in your ascent of nearly 1500 ft!
Here you discover your first glimpse of the coast from the nearby peak of Roseberry Topping, the result being awe-inspiring, panoramic views at 1050ft.
From North York Moors to the Cleveland Heritage Coast
From the moors, the route drops to converge with the coastal path driving south along the rugged cliff top paths and bays of the Yorkshire coast. This is part of the Cleveland Heritage Coast, where the wild heather of the moors now start to peer over the cliffs edge.
From the historic seaside towns of Whitby and Robin Hood’s Bay, you have amazing views out into the North Sea-ending your walk on the coast at Filey Brigg, 7 miles south of Scarborough.
Walk the Cleveland Way and witness for yourself the great beauty of the diverse moorland and coast. Significant historical events are embedded deep into the moors heritage - evident in the area famous abbeys and castles. We stay over night in moorland villages and coastal ports, celebrated for their local cheese and ale. Here, you can make the most of the excellent B&B’s and Inns, as well as the famous Yorkshire hospitality.
The contrast in scenery is what makes the Cleveland Way totally unique – no other long distance path combines moor and coast so well.
For more information and advice on walking the Cleveland Way, please call our walk team who will be delighted to help you with your holiday plans.
Celtic Trails Walking Holidays has 20 years’ experience providing tailored, high quality itineraries for walkers who appreciate good service, comfort and organisation.
Path Walkthrough
Our Cleveland Way Walking Holiday route leads from Helmsley to the coast at Filey
In terms of scenery, this route offers a great sense of diversity in landscape. By and large, this is a walk through moorland to the coast, with its fishing villages overlooking the North Sea. Through the North York Moors National Park you'll trek over heather-capped hills, with far-reaching views over the surrounding area from the ridge at Hambleton hills and Roseberry Topping.
Whereas some sections over the moors will involve ups and downs, the path along the coast also becomes quite steep in places (especially on the section towards Robin Hood Bay). These sections become harder to negotiate in wet weather, but are not too challenging providing you have the right footwear and waterproof clothing for the weather. However, navigation shouldn't be a problem as the route is amply way-marked, and well connected with a local bus service running alongside the majority of the path.
Walk Gallery
Our Cleveland Way Walking Holiday Itineraries
Prices are per person, based on 2 people sharing, single person supplements apply.
Solo walker supplement: £40 (pn) Single occupancy (groups): £30 (pn)
Day
Locations
Distance
Day 12:
Depart Filey
Day 1:
Arrive Helmsley
Day 2:
Helmsley to Sutton Bank
10 miles/16km
Day 3:
Sutton Bank to Osmotherley
11.25 miles/18km
Day 4:
Osmotherley to Clay Bank Top
11 miles/17.5km
Day 5:
Clay Bank Top to Roseberry Topping
13.5 miles/21.6km
Day 6:
Roseberry Topping to Saltburn by Sea
10.5 miles/17km
Day 7:
Saltburn by Sea to Staithes
8.8 miles/14.1km
Day 8:
Staithes to Whitby
11.6 miles/18.5m
Day 9:
Whitby to Robin Hood’s Bay
7 miles/11.2km
Day 10:
Robin Hood’s Bay to Scarborough
14 miles/22.4km
Day 11:
Scarborough to Filey
10.5 miles/16.8km
Itinerary Information: 11 nights accommodation with 10 walking days. Arrive in Helmsley on day 1, walk from day 2 and depart from Filey on morning of day 12.
Departure Dates: This itinerary can be walked any time between Mar to Oct. You simply choose which day you would like your holiday to start on.
Rest Days: Should you wish, rest days can be taken at stops along the route, view details.
Solo walker supplement: £40 (pn) Single occupancy (groups): £30 (pn)
Day
Locations
Distance
Day 11:
Depart Filey
Day 1:
Arrive Helmsley
Day 2:
Helmsley to Sutton Bank
10 miles/16km
Day 3:
Sutton Bank to Osmotherley
11.25 miles/18km
Day 4:
Osmotherley to Clay Bank Top
11 miles/17.5km
Day 5:
Clay Bank Top to Kildale
9 miles/14.4km
Day 6:
Kildale to Saltburn by Sea
14.75 miles/23.6km
Day 7:
Saltburn by Sea to Runswick Bay
12.2 miles/20.5km
Day 8:
Runswick Bay to Robin Hood’s Bay
15.2 miles/24.3km
Day 9:
Robin Hood’s Bay to Scarborough
14 miles/22.4km
Day 10:
Scarborough to Filey
10.5 miles/16.8km
Itinerary Information: 10 nights accommodation with 9 walking days. Arrive in Helmsley on day 1, walk from day 2 and depart from Filey on morning of day 11.
Departure Dates: This itinerary can be walked any time between Mar to Oct. You simply choose which day you would like your holiday to start on.
Rest Days: Should you wish, rest days can be taken at stops along the route, view details.
Single occupancy supplement within a group: £30 per night. Where singles are walking as part of a larger group and are willing to share a Walk Pack, single room occupancy supplements apply.
Rest days: From £50 per person per night.
Postage overseas: £5.00 (Europe), £10.00 (Rest of the World) per walk pack
Bank holidays & short notice bookings may incur extra charges.
We advise taking this route between March and October as the winter months can bring windy and unsettled weather around the moors, making progress along this route more difficult.
The path around the coast is liable to become quite muddy following wet weather, in any case its better to be prepared with good, sturdy footwear and waterproofs for this hike.
Walker Reviews of Our Cleveland Way Walking Holidays
Our past clients rated this walk 4.8 out of 5; read a selection of 12 reviews below.
Celtic Trails are up there with the best - we would walk with you again, no problem.
The accommodations were all very good and we most enjoyed the freedom and the variety.
4.5 out of 5
J&M Orchard July 2018
This holiday was great - very empowering. Most enjoyed the moors - even in rain/fog.
5 out of 5
M. McClean September 2019
We would recommend Celtic Trails to a friend; very good organisation and very good follow up.
5 out of 5
Anon June 2019
We enjoyed our holiday tremendously - particularly the variety of going from the moors to the coast.
We have walked with you a few times before and you have met our expectations again
5 out of 5
C&S Ungar October 2018
Excellent walk - well marked and maintained.
Good B&Bs. Where next …???
5 out of 5
R&M July 2018
We have used you before and we would use you again, as we like the standard of accommodation.
5 out of 5
Ferris July 2018
"Used before, would use again, we like the standard of accommodation."
5 out of 5
Ferris July 2018
With great thanks for your thoughtful attention to our particular needs.
5 out of 5
B&D Gwaltney June 2018
"We have been happy with our walk, from initial contact to the end, it all went really well. I feel [other companies] are not paying attention to detail, we will use Celtic Trails again."
4 out of 5
Williams October 2017
"Supa! Keep up the good work. We enjoyed the beauty of the scenery, then a nice shower and a warm bed (as well as a good meal and a good beer)."
4.8 out of 5
De Deken & Peetas August 2016
"Great walking holiday! Particularly liked the combination of moorland and coastal walking. Have walked with another other company but several now with Celtic Trails - you would be our first preference!!"
5 out of 5
Read & Raco September 2015
"Dear Penny, we would like to thank you for a great holiday. We would happily stay at any of the accommodations again! All your organisation of the accommodation and luggage worked smoothly and we were free to just enjoy the walking. The Cleveland Trail is very well signed ~ we did actually complete the walk to Filey.
Thanks again."
4.7 out of 5
Bowles May 2015
Leave your own review of your Cleveland Way Walking Holiday with us here
Enquire About Cleveland Way
Booking Request - Cleveland Way
What Happens Next?
We will check your details and come back to you within two working days with a personalised estimate based on your requirements. We will then formally request a deposit of £100 per person (£150 for solo walkers) and book all your arrangements - find out about our full booking porcess here.
Please note this does not constitute a booking confirmation, we kindly ask you to refrain from booking any travel until we have confirmed all your arrangements.
Still Have Questions?
If you are still unsure on any of your requirements, please do enquire with us first and one of our friendly team will be happy to help you with any queries you have.
eveland Way lies within the National Park, the largest area of moorland in England before reaching the North Sea coast.
