Walking Diverse Landscape on the Cleveland Way

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
  • 10 to 11 nights
  • 110 mls (view km)
  • Helmsley, Northern England
  • Moderate
  • Mar to Oct
  • £785

Walking The Cleveland Way

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 ClStaithes Fishing village Ceveland Wayeveland 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

Cleveland Way walking map
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 two people sharing, single person supplements apply.

Helmsley to Filey

Length: 110.5 miles/176 km | Difficulty: Moderate

CodeDurationStart Price 
CLV111 nights, 10 days£845 (pp)View Itinerary
CLV210 nights, 9 days£765 (pp)View Itinerary

Helmsley to Filey

Eleven nights, Ten days
Price: £845 (pp)
Solo walker supplement: £35 (pn)
Holiday Code: CLV1
DayLocationsDistance
Day 12:Depart Filey
Day 1:Arrive Helmsley
Day 2:Helmsley to Sutton Bank10 miles/16km
Day 3:Sutton Bank to Osmotherley11.25 miles/18km
Day 4:Osmotherley to Clay Bank Top11 miles/17.5km
Day 5:Clay Bank Top to Roseberry Topping13.5 miles/21.6km
Day 6:Roseberry Topping to Saltburn by Sea10.5 miles/17km
Day 7:Saltburn by Sea to Staithes8.8 miles/14.1km
Day 8:Staithes to Whitby11.6 miles/18.5m
Day 9:Whitby to Robin Hood’s Bay7 miles/11.2km
Day 10:Robin Hood’s Bay to Scarborough14 miles/22.4km
Day 11:Scarborough to Filey10.5 miles/16.8km

Itinerary Information: Eleven nights accommodation with ten walking days. Arrive in Helmsley on day one, walk from day two and depart from Filey on morning of day twelve.

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.

What's Included: view full details.

Back to all itineraries

Helmsley to Filey

Ten nights, Nine days
Price: £765 (pp)
Solo walker supplement: £35 (pn)
Holiday Code: CLV2
DayLocationsDistance
Day 11:Depart Filey
Day 1:Arrive Helmsley
Day 2:Helmsley to Sutton Bank10 miles/16km
Day 3:Sutton Bank to Osmotherley11.25 miles/18km
Day 4:Osmotherley to Clay Bank Top11 miles/17.5km
Day 5:Clay Bank Top to Kildale9 miles/14.4km
Day 6:Kildale to Saltburn by Sea14.75 miles/23.6km
Day 7:Saltburn by Sea to Runswick Bay12.2 miles/20.5km
Day 8:Runswick Bay to Robin Hood’s Bay15.2 miles/24.3km
Day 9:Robin Hood’s Bay to Scarborough14 miles/22.4km
Day 10:Scarborough to Filey10.5 miles/16.8km

Itinerary Information: Ten nights accommodation with nine walking days. Arrive in Helmsley on day one, walk from day two and depart from Filey on morning of day eleven.

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.

What's Included: view full details.

Back to all itineraries

  • What's Included

    We include:

    • Good standard accommodation at a mixture of Guesthouses, Farmhouses, local Inns and B&B’s with ensuite or private facilities wherever possible
    • Breakfast
    • Luggage transfers (one bag per walker, max 18kg per bag)
    • Personal transfer between accommodation and path where necessary
    • Route planning
    • Walk Pack including Trail Guide, itinerary, accommodation directions, local interest leaflets and holiday planning
  • Price Info.

    Bank Holidays & Short notice bookings may incur extra charges.

    Rest Days From £45.00 pp per night

    Single supplements

    Solo person bookings: £35.00 per night

    Where singles are walking as part of a larger group and are willing to share a Walk Pack: single room occupancy supplements will apply.

    Postage Overseas: £5.00 (Europe), £10.00 (Rest of the World) per walk pack

  • Getting There

    Travel arrangements for arrival/departure

    Nearest major airports are located in Manchester and Newcastle.

    Railway stations are located in York, Scarborough and Filey.

    www.nationalrail.co.uk

    There is a bus from York to Helmsley.

    If you prefer to arrive by car, we can advise on car parking arrangements.

    Taxi 

    Approx. taxi fares:

    Thirsk to Helmsley - £40

    Filey to Helmsley - £60

  • Best Time to Travel

    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.

    Average Daylight on Walking The Cleveland Way                                                            Average Rainfall Weather Conditions for Walking The Cleveland Way                                                 Average Temperatures Walking The Cleveland Way

Walker Reviews of Our Cleveland Way Walking Holidays

Our past clients rated this walk 4.7 out of 5, read a selection of 5 reviews below.

"Used before, would use again, we like the standard of accommodation."

5 out of 5

July 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

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

August 2016

"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

May 2015

"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

September 2015

Leave your own review of your Cleveland Way Walking Holiday with us here

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