10 to 11 nights
110 mls (km)
Northern England
Moderate
Mar to Oct
£955

Walking Diverse Landscape on the Cleveland Way

  • 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
Staithes Fishing village cCeveland Way

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 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.

Hiking holidays Cleveland Way

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.

Cleveland Way walking map
Our Cleveland Way Walking Holiday route leads from Helmsley to the coast at Filey

Path Walkthrough

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.

Our Cleveland Way Itineraries

  • Helmsley to Filey
    Distance: 110 miles (177km)
    CLV1
    11 Nights, 10 Days
    from £1030 pp
    CLV1 ~ Helmsley to Filey ~ 11 / 10 classic
    DayLocationsDistance
    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
    Day 12:Depart Filey


    or ask us a question
    What's Included:
    10 walking days
    11 nights accommodation
    11 breakfasts
    + all our usuals
    Prices
    Extras
    <~ Go back to all itineraries
    CLV2
    10 Nights, 9 Days
    from £955 pp
    CLV2 ~ Helmsley to Filey ~ 10 / 9 classic
    DayLocationsDistance
    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 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
    Day 11:Depart Filey


    or ask us a question
    What's Included:
    9 walking days
    10 nights accommodation
    10 breakfasts
    + all our usuals
    Prices
    Extras
    <~ Go back to all itineraries
    • Classic Grade:  a good standard accommodation at a mixture of Guesthouses, Farmhouses, local Inns and B&B’s with en-suite or private facilities wherever possible
    • Breakfast
    • Luggage transfers (one bag per walker, max 18kg per bag)
    • Route planning
    • Walk Pack including
      • Trail Guide,
      • itinerary,
      • accommodation directions,
      • local interest leaflets
      • holiday planning

    You choose which day you would like your holiday to start on. We will book your holiday in accordance with your requirements.

    Our Cleveland Way holidays are available to walk March to October.

    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.

    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.

    Taxis can be organised - prices available upon request.

    Looking for different mileages or a different number of nights? Please contact us to discuss how our itineraries can be adjusted to meet your specific needs. Call one of our helpful team on +44 (0)1291 689774 or e-mail us here.

    Cleveland Way Client Reviews

    4.9/5 based on 18 reviews
    Quality advice. Trustworthy booking. Everything happens as promised. Always there if required. Good to deal with.
    - July 2021
    Celtic Trails were easy and efficient. It was good to get away after the pandemic.
    - June 2021
    Overall, we had a great holiday - I'm pleased we went with Celtic Trails. I would describe them as very efficient. Excellent information, took all the 'admin' out of doing the walking, leaving us to enjoy it more. A lovely scenic walk.
    - May 2021
    Efficient, good accommodation bookings and details.
    - September 2019
    Celtic Trails are very efficient and thorough; they are the easyway to do a long distance walk.
    - September 2019
    Celtic Trails are much better than other companies - very easy to use, very good accommodations, excellent information. Cleveland Way is very well maintained and a thoughtfully planned walk.
    - September 2019
    This holiday was great - very empowering. Most enjoyed the moors - even in rain/fog.
    - September 2019
    We would recommend Celtic Trails to a friend; very good organisation and very good follow up.
    - 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
    - October 2018
    Excellent walk - well marked and maintained. Good B&Bs. Where next …???
    - July 2018
    We have used you before and we would use you again, as we like the standard of accommodation.
    - July 2018
    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.
    - July 2018
    With great thanks for your thoughtful attention to our particular needs.
    - 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."
    - 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)."
    - 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!!"
    - 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."
    - May 2015
    Celtic Trails sort out the practicalities so you can focus on and enjoy the walk and rests in between. Feel a great sense of achievement from this holiday. The contract between the moors, woods and coastline was fabulous. We wish we'd scheduled a rest day.
    - January 1970
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    Booking Request - Cleveland Way
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    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 £150 per person (£100 per person for a single centre break) and book all your arrangements - find out about our full booking process 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.

    Enquire About Cleveland Way
    +44 (0)1291 689 774
    Our lines are open: 9am to 5pm (GMT), Monday to Friday
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    Sample Accommodations

    Please note: exact accommodation booked will depend on availability.