10 to 11 nights
110 mls (km)
Northern England
Moderate to Challenging
Mar to Oct
£1355

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 hikes 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 1050 ft.

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 starts to peer over the cliff edge.

From the historic seaside towns of Whitby and Robin Hood’s Bay, you have amazing views out to 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 within the moors heritage - evident in the area's famous abbeys and castles.

We stay overnight in moorland villages and coastal ports, celebrated for their local cheese and ale. Here, you can make the most of the excellent B&Bs 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 friendly walk team who will be delighted to help you with your holiday plans.

Celtic Trails Walking Holidays has over 27 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's 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 £1495 pp
    Helmsley to Filey
        11 nights, 10 days
    Ref: CLV1
    Moderate,
    Grade: Classic
    CLV2
    10 Nights, 9 Days
    from £1355 pp
    Helmsley to Filey
        10 nights, 9 days
    Ref: CLV2
    Moderate, Moderate to Challenging,
    Grade: Classic
    • Good standard accommodation at a mixture of guesthouses, farmhouses, local inns and B&Bs with en-suite or private facilities wherever possible
    • Breakfast
    • Luggage transfers
    • Personal transfer between accommodation and path that form a part of our standard package
    • Route planning
    • Walk pack including Trail Guide and mapping, itinerary, accommodation directions and route notes, lunch and dinner information, restaurant recommendations and holiday planning details

    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 path around the coast is liable to become quite muddy following wet weather, in any case it's better to be prepared with good, sturdy footwear and waterproofs for this hike. We suggest walking this route between March and October.

    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

    4.8/5 based on 39 reviews
    Celtic trails are very professional and well organised
    - September 2024
    As a single walker I feel really safe and well looked after and I love the flexibility to book rest days. A walking holiday with no worries, I can just wake up and start walking to my next destination and arrive happy and you can be sure to stay in lovely accommodations. Thank you Celtic Trails.
    - July 2024
    Perfect and very friendly and swift service.
    - June 2024
    Celtic Trails were reliable, supportive, good service. Good selection of walks. CT selects some fun places to stay, good adventure
    - June 2024
    Celtic Trails are always a pleasure to deal with. The Cleveland Way is the longest walk I have done and was a true challenge for me which I am so pleased and proud to have risen to.
    - June 2024
    Another excellent holiday with Celtic Trails. Thank you.
    - May 2024
    Celtic Trails are an excellent company. They organised all the accommodations, which were upper end of the market, all luggage transfers and taxis to and from the trail. They gave us a brilliant folder with all the information needed about our accommodations each day and where to get food etc.
    - April 2024
    Very good - extremely efficient, good attention to details. Overall excellent
    - March 2024
    This was our fourth time (I think) that we have used your company and every time we have been very pleased with the initial website, the booking process and the documents that you supply. The follow up and support has been second to none. We have recommended Celtic Trails to a number of other hikers.
    - September 2023
    This is the second time I?ve planned a walk with Celtic Trails and the details matter, so thanks for that. The walk pack, details, booking and luggage transfer were without error, this really matters when you are out on a hike and tired as you come into your accommodation. The accommodations were good, clean, warm and in the local character. I totally recommend it. I have done many various holiday trips, though I find getting out in the countryside, experiencing the views, the smells, the sounds, the activity and ?nature tranquillity? to be very therapeutic; great for the body, mind and soul. I really try to be present and in the moment on trips like this. ????
    - May 2023
    Celtic Trails are very efficient. Would recommend.
    - September 2022
    Cleveland Way was a walk of two halves. Awesome to visit the moors, and the contrast of sitting on a beach. Celtic Trails' Walk Pack are brilliant. All the hassle taken away. Excellent customer service.
    - August 2022
    Celtic Trails provided a first-class service with personal touch - perceived as more than just a booking reference. We enjoyed the variety of this trail - something for everyone. Well sign-posted and enough ascents / descents to challenge.
    - July 2022
    I would say that Celtic Trails is very well organised and their customer service is excellent. I would like to thank Penny fore being absolutely wonderful when we hit a snag with our luggage being transferred. I was so impressed when she arranged for a cab to pick up and deliver all of our bags within an hour. My family was incredibly grateful! Penny is awesome!
    - June 2022
    Celtic Trails were very good; well organised, flexible service and good standard of accommodation. Thanks, Penny - we had a great time. And thank you for rolling over our holiday from pre-Covid times without penalty - much appreciated. This walk had an
    - May 2022
    Celtic Trails makes the walk wonderful and planning for the trip easy. They take care of all the details, so we could focus on having fun and relaxing.
    - April 2022
    Celtic Trails were efficient and professional, providing a good holiday. It was good to be able to enjoy such a holiday again after the pandemic. The Cleveland Way is a lovely part of the country, which we were not familiar with.
    - October 2021
    Helpful staff. Excellent accommodation chosen. Good information supplied. Very reasonable price for the standard of accommodation. Great to be somewhere new. First holiday for 2 years owing to Covid and we were so lucky with the weather. This walk has a wonderful variety of scenery and was just the right amount of challenging.
    - September 2021
    Really impressed. You are friendly and approachable and sorted a minor issue promptly. Thank you. Better than other companies. I have wanted to walk the Cleveland way for some years. I most enjoyed the variety of countryside, the incredible views and the wildlife. Walking is my greatest pleasure.
    - September 2021
    A good mix of inland and coast walking. We felt a great sense of achievement. Celtic Trails were well organised.
    - September 2021
    Walk Pack was better than other companies and standard of accommodation was higher, but I I'm uncomfortable walking on cliffs for extended periods.
    - September 2021
    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 rest in between. Feel a great sense of achievement from this holiday. The contrast between the moors, woods and coastline was fabulous. We wish we'd scheduled a rest day.
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