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Cleveland Way Walking Holiday

The Cleveland Way

  • Walk the Cleveland Way from the North York Moors to the North Sea
  • Step back in time visiting Whitby Abbey, Rievaulx Abbey and Scarborough Castle
  • Follow trails through remote moorland in an iconic Yorkshire landscape
  • Admire the unique views to the Cleveland Heritage Coast from Roseberry Topping
  • Explore charming Victorian seaside villages - Whitby, Scarborough and Filey

Walking the Cleveland Way combines the remote nature of the North York Moors with the rugged Cleveland Heritage Coast, the best of two very distinct landscapes. This National Trail punches well above its weight with its variety of walking, scenery and history. 

Connect with the rich heritage of Northern England and visit important historical sites such as Helmsley Castle, Mount Grace Priory and Rievaulx Abbey. The Cleveland Way hugs the coastline, following high cliffs and visiting charming seaside towns such as Robin Hood’s Bay, Whitby and Filey. Here you can listen to the tales of smugglers and saints whilst enjoying a refreshing local pint. Spot the variety of wildlife, from the singing seabirds on the coast to grouse hiding in the moors. The waymarking on this long-distance trail is excellent, taking you through green forests, along the dramatic North Sea Coast and rewarding you with far-reaching views to the Cleveland Hills. 

Macs Adventure has been organising adventures along the Cleveland Way since 2003. Having operated this trip for close to two decades, we know the area and our accommodations along this route very well. Enjoy the ease of having your luggage transferred each day, and the personal touch of the small, family-run accommodations that we choose.

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Discover The Cleveland Way

  • Why book the Cleveland Way with Macs Adventure?

    When Macs Adventure first began in 2003, we launched a couple of walking routes including the West Highland Way and Hadrian's Wall Path. These trips were the ones we originally sold, and after their success, we very quickly decided to expand our product range and added the little-known Cleveland Way.

    This hike is reasonably close to home which enabled us to get there, meet the accommodation owners and make sure the trail was as good as we had heard. The fact that 16 years later we still sell it to happy customers every year speaks volumes. The bonus of some of the greatest moor walking in the UK and the rugged North Sea Coast made the route a must-do for us.

    In 2019 we celebrated its 50th anniversary, and we sent Ben Lerwill, a journalist for The Times, out to walk the route and discover the delights of the Cleveland Way's 110 miles. The result was a fantastic article which you can read here.

    We love the Cleveland Way and our main aim is to make sure that you do too.

    Why book the Cleveland Way with Macs Adventure?
  • Cleveland Way FAQ's

    Q: How fit do I need to be?

    A: Depending on your itinerary the grade of this trip is either easy to moderate (11 Days), or moderate to strenuous (9 Days). There are some uphill sections along the coast near Robin Hood's Bay and in the moors, where Urra Moor (1490ft) and Roseberry Topping (1050ft) are the highest points. This trip is suitable for both regular walkers and first-timers.

    Q: When is the best time of year to go?

    A: We offer the Cleveland Way from April to October. If you would like to see the moorland heather in bloom it is best to go during the months of August or September. Traditionally, April and May have been the most popular time of the year to walk the route, as the theory goes that the weather is better. 

    Q: Will I need a map and compass?

    A: The Cleveland Way is very well waymarked and no great navigation skills are required. As well as a detailed information pack you can download the Macs Adventure smartphone app to navigate and track your progress along the route. This way you will have a safe, enjoyable and problem-free trip!

    Q: How do the baggage transfers work? 

    A: Enjoy the ease of having your luggage transferred daily, allowing you to walk with just a light daypack and your packed lunch. Your bags will be transferred from your accommodation as per your itinerary and moved on to your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.

    Cleveland Way FAQ's
  • The Cleveland Way's Points of Interest
    • Whitby Abbey - The remains of Whitby Abbey are perched high on a cliff, offering outstanding views everywhere you look – across the harbour and into the rolling countryside. There are years of history to discover as you wander around the ancient ruins that were the inspiration for Bram Stoker’s gothic tale of ‘Dracula’.

    • Robin Hood's Bay - Hunt for ancient fossils on the sandy beach, wander through its cobbled streets and visit the friendly cafes, pubs, and restaurants. Relax with refreshing homemade ice cream as you learn about the local history of smugglers, sailors and fishermen that walked the same streets hundreds of years ago.

    • Roseberry Topping - Also known as Yorkshire’s very own Matterhorn! Although Roseberry Topping is not actually a mountain (pictured), it makes for an exciting experience. Once you reach the summit you are rewarded with views to the surrounding countryside and the coast.  

    • Helmsley Brewery - This family-run brewery has a mission ‘to make other people as passionate about handcrafted beer from the North Yorkshire Moors’ and offers tours and tastings. All beers contain Yorkshire Malts and at least one English hop, the perfect way to celebrate the start of your adventure!
    The Cleveland Way's Points of Interest


Reasons to believe in Macs Adventure:
The Biggest Choice

The Biggest Choice

Self-guided walking & cycling is all we do - we have hundreds of tried & tested trips.
Our Heritage

Around Since 2003

We’re still founder led & the world’s number one self-guided operator with mountains of experience.

21,000+ Customer Reviews

Plus, with a Feefo Platinum Service Award & British Travel Awards, you know you're in good hands.
Positive Impact

Positive Impact

We use independent suppliers to support communities along our routes, as well as work with organisations to help maintain & restore paths.
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