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25,000+ trip reviews, with an average rating of 4.8 out of 5.
Starts
Ends
Helmsley, England
Filey, England
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Bracing Walking on North Yorkshire Trails
A Mix of Coastal and Moorland Walks
Much Historical Interest
Complete a Real Challenge, Without Things Being Too Challenging!
The Cleveland Way walking trip is a 12-day journey through the varied landscapes of northern England, tailored for experienced and senior walkers seeking moderate adventure. Starting in Helmsley and ending in Filey, the trail combines rolling moorlands with the dramatic Yorkshire Heritage Coast. Explore historic sites like Rievaulx Abbey, the Captain Cook Monument, and Whitby Bay, famous for its fish and chips. The route, established as a National Trail in 1969, features a mix of tranquil farmland, forested patches, and charming fishing villages. The tour’s standout aspect is its seamless blend of coastal and moorland walking, offering both scenic beauty and a taste of local history.
Walking the Cleveland Way was a wonderful experience. The variety of countryside, moorland and coast, makes it extra special. The accommodation along the way was high quality with friendly hosts, and the luggage service worked like a dream. We met so many lovely walkers along the way and often dined with them in the evenings. It was such a special trip.
