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Cleveland Way Hiking Tours

The Cleveland Way is a 109-mile National Trail that loops through North Yorkshire, tracing the edge of the North York Moors before turning south along the Cleveland Heritage Coast. Macs Adventure runs it self-guided, from Helmsley to Filey, with everything arranged for you.

Walk moorland ridges above Rosedale and Farndale, drop into fishing villages like Robin Hood's Bay, and pass beneath the ruins of Whitby Abbey and Scarborough Castle on the coastal half of the route. Shorter sections and full end-to-end itineraries are both available.

20+ years planning self-guided trips across England's National Trails - Macs Adventure is the world's #1 self-guided hiking operator.

Why choose Cleveland Way Hiking Tours

Why the Cleveland Way rewards a self-guided hiker

  • Horseshoe route

    A horseshoe route where moorland walking gives way to 50 miles of dramatic coastline

  • Whitby and Robin Hood's Bay

    Passes Whitby Abbey's ruins and the working harbor at Robin Hood's Bay

  • National Trail

    One of England's original National Trails, waymarked throughout with the acorn symbol

  • Full or part

    Choose the full 109-mile end-to-end route or a shorter coastal or moorland section

  • Luggage transfers

    Luggage transfers are arranged between stops where listed in your itinerary.

  • England

    Cleveland Way

    Walk between historic villages on a trail of contrasts, from high cliff tops to wild moorland

    • Walking
    • 11 days
    from$3,595CAD pp
    View Route
  • England

    Dales Way

    Cross two national parks as you make your way from the Yorkshire Dales to Lake Windermere.

    • Walking
    • 8 days
    from$2,720CAD pp
    View Route
  • England

    Yorkshire Dales In Comfort

    Classic walking through the Dales, staying in charming Yorkshire villages and towns

    • Walking
    • 6 days
    from$1,915CAD pp
    View Route
  • England

    The Herriot Way

    A circular walk through James Herriot's Yorkshire, a land of rolling dales and heather-clad moorland

    • Walking
    • 6 days
    from$1,985CAD pp
    View Route
  • England

    Discover England: The Lake District to Yorkshire Dales

    Discover England's North, journey through the Lake District and Yorkshire Dales by rail and on foot!

    • Walking
    • 8 days
    from$3,005CAD pp
    View Route
  • England

    Coast to Coast Walk

    Hike Alfred Wainwright's famous Coast to Coast, one of the world's great walks.

    • Walking
    • 9–18 days
    from$2,795CAD pp
    View Route
  • England

    Northumberland Coastal Path

    A classic walking holiday along the deserted beaches of the Northumberland Coast to the Holy Island

    • Walking
    • 5 days
    from$1,480CAD pp
    View Route
  • England

    Pennine Way

    Walk the UK's first National Trail through the Peak District, Yorkshire Dales and Northumberland.

    • Walking
    • 21 days
    from$8,275CAD pp
    View Route
  • England

    Hadrian's Wall Walk

    Roman history, wild Northumberland moorland and a warm northern welcome—hike Hadrian’s Wall your way.

    • Walking
    • 5–10 days
    from$1,455CAD pp
    View Route
  • England

    The Lake District Trail

    Walk from the shores of Windermere through the rugged Central and Eastern fells to Keswick.

    • Walking
    • 5–7 days
    from$1,620CAD pp
    View Route

Get to know Cleveland Way Hiking Tours

  • When to go

    May to September is best - moorland heather blooms purple in August, and coastal sections stay clear of winter storms. July and August are busiest on the coast path around Whitby.

  • What the trail is actually like

    Two distinct halves - inland moorland tracks with long views over Rosedale and Farndale, then a coast path with steep dips into fishing villages like Staithes and Robin Hood's Bay.

  • Where you will stay

    Traditional coaching inns and family-run B&Bs in market towns and fishing villages - Helmsley, Whitby, Scarborough and Filey among them.

  • How fit do I need to be

    Moderate fitness. Daily distances of 10-15 miles with real ascent on the moorland stages and some steep coastal dips near Whitby and Robin Hood's Bay.

Get inspired for Cleveland Way Hiking Tours

  • Tips & Advice

    Frequently Asked Questions About England's Cleveland Way

    There are some considerations when walking the Cleveland Way and our team of experts have come up with the questions they are most frequently asked.

    Read blog

  • Hiking

    A Complete Guide to Hiking in Yorkshire

    Discover the best Yorkshire hikes and travel tips. Learn about the Yorkshire Dales, Moors, and coast. Explore self-guided hiking trips with Macs Adventure!

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  • Hiking

    Best Hikes in Yorkshire

    Discover the best hikes in Yorkshire, including Yorkshire Dales National Park walks. Explore self-guided hiking tours with Macs Adventure. Plan your trip today! 

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Know before you go