Cleveland Way - England

Price per person from:

£498

Walking holidays and hiking tours on the Cleveland Way
Itinerary Options: 5-10 days


The Cleveland Way is a gorgeous walking holiday in the North York Moors National Park. Beautifully situated in the north east of England. The Cleveland Way is also a National Trail of wonderful variety. Starting in... Read more below



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Cleveland Way - England

Cleveland Way

The Cleveland Way is a gorgeous walking holiday in the North York Moors National Park. Beautifully situated in the north east of England. The Cleveland Way is also a National Trail of wonderful variety. Starting in Helmsley, the Cleveland Way is around 108 miles long, and has two distinct sections. Inland walking, and coastal walking. Roughly half of this National Trail crosses attractive farmland, woods, and the beautiful heather moorlands of the North Yorkshire Moors. From Helmsley through to Saltburn-by-the-Sea you walk the inland section. From there on the walk remains coastal. Dramatic cliff tops, former fishing villages, and a fabulous coastline all the way to Filey. A walking holiday that has the lot!

The Cleveland Way was the second National Trail in England and Wales and was officially opened in 1969. Anyone who is reasonably fit can walk The Cleveland Way. It can be challenging in some sections, especially along the coast, but this just adds to the rewarding overall experience. Just choose an itinerary that looks comfortable, and you will have a truly super holiday.

The Cleveland Way is managed by the National Trails partnership. This means that the area you are walking has been well maintained, and you are going to be in a beautiful walking area. You follow the famous ‘white acorn’ symbol, which is on posts and stiles along this delightful route. There is a wonderful sense of history here, probably due to its remoteness and being a designated National Park. The Moors have been saved from change largely by altitude and land ownership. A rich assortment of Stone age and Bronze age burial forts, Norman Abbeys and Castles are dotted along the route.

When can I walk this trail? Well, anytime of the year is good for this particular route. We mostly offer our holidays between March and October. The weather and daylight hours are far better at that time of year too. If you want to see the moorland heather in bloom, then August/September is best. The route itself is a horseshoe shape. It skirts around the North York Moors National Park. Then onto the visual feast which is the dramatic North Yorkshire coastline. Helmsley Castle, Rievaulx Abbey, Mount Grace Priory, Gisborough Priory, Whitby Abbey and Scarborough Castle are just a few special sites of interest on this fabulous walk.

When you are not admiring the view, look to your feet. The changing geology as you walk along the length of this trail will display well drained limestone of the Tabular Hills north of Sutton Bank. The moorland is formed by an enormous block of acid sandstone exposing sandy orange pathways. Picturesque cottages are constructed from local limestone and sandstone.

A walking holiday on the Cleveland Way can be taken as a whole, or split into 2 sections. With varied walking itineraries from 6 to 11 days there is sure to be a walking holiday to suit you. Other holidays we offer in the north of England are the Hadrians Wall Path, The Pennine Way, The Coast to Coast Walk, and many more!

The Red Grouse is a bird native to Britain. It is only found amongst heather plants on the Moorland. You may be lucky and see some. Beautiful wild flowers adorn this route.


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  • Holiday code
    Start and Finish Point
    Duration of stay
    Price PP (2 sharing)
    Download Itinerary
    Book Holiday
    More Info
  • CLEVW10
    Helmsley to Filey
    10 nights / 9 days
    £779.00
    • CLEVW10
    • Helmsley to Filey
    • 10 / 9
    • 108 / 174
    • £779.00
    • Helmsley
    • Helmsley to Sutton Bank
      10 / 16

    • Sutton Bank to Osmotherley
      11 / 18

    • Osmotherley to Clay Bank Top
      11 / 18

    • Clay Bank Top to Kildale
      9 / 14

    • Kildale to Saltburn-by-the-Sea
      15 / 24

    • Saltburn-by-the-Sea to Runswick Bay
      12 / 19

    • Runswick Bay to Robin Hoods Bay
      14 / 23

    • Robin Hoods Bay to Scarborough
      12 / 19

    • Scarborough to Filey
      11 / 18

    • Filey
  • CLEVW11
    Helmsley to Filey
    11 nights / 10 days
    £849.00
    • CLEVW11
    • Helmsley to Filey
    • 11 / 10
    • 108 / 174
    • £849.00
    • Helmsley
    • Helmsley to Sutton Bank
      10 / 16

    • Sutton Bank to Osmotherley
      11 / 18

    • Osmotherley to Clay Bank Top
      11 / 18

    • Clay Bank Top to Roseberry Topping
      13 / 21

    • Roseberry Topping to Saltburn-by-the-Sea
      10 / 16

    • Saltburn-by-the-Sea to Staithes
      9 / 14

    • Staithes to Whitby
      11 / 18

    • Whitby to Robin Hoods Bay
      6 / 10

    • Robin Hoods Bay to Scarborough
      12 / 19

    • Scarborough to Filey
      11 / 18

    • Filey
  • CLEVW8
    Helmsley to Filey
    8 nights / 7 days
    £645.00
    • CLEVW8
    • Helmsley to Filey
    • 8 / 7
    • 108 / 174
    • £645.00
    • Helmsley
    • Helmsley to Osmotherley
      21 / 34

    • Osmotherley to Clay Bank Top
      11 / 18

    • Clay Bank Top to Roseberry Topping
      13 / 21

    • Roseberry Topping to Staithes
      19 / 31

    • Staithes to Robin Hoods Bay
      17 / 27

    • Robin Hoods Bay to Scarborough
      12 / 19

    • Scarborough to Filey
      11 / 18

    • Filey
  • CLEVWC6
    Saltburn-by-the-Sea to Filey
    6 nights / 5 days
    £498.00
    • CLEVWC6
    • Saltburn-by-the-Sea to Filey
    • 6 / 5
    • 49 / 79
    • £498.00
    • Saltburn-by-the-Sea
    • Saltburn-by-the-Sea to Staithes
      9 / 14

    • Staithes to Whitby
      11 / 18

    • Whitby to Robin Hoods Bay
      6 / 10

    • Robin Hoods Bay to Scarborough
      12 / 19

    • Scarborough to Filey
      11 / 18

    • Filey
  • CLEVWM6
    Helmsley to Saltburn-by-t...
    6 nights / 5 days
    £498.00
    • CLEVWM6
    • Helmsley to Saltburn-by-the-Sea
    • 6 / 5
    • 56 / 90
    • £498.00
    • Helmsley
    • Helmsley to Sutton Bank
      10 / 16

    • Sutton Bank to Osmotherley
      11 / 18

    • Osmotherley to Clay Bank Top
      11 / 18

    • Clay Bank Top to Roseberry Topping
      13 / 21

    • Roseberry Topping to Saltburn-by-the-Sea
      10 / 16

    • Saltburn-by-the-Sea
  • CLVW9
    Helmsley to Filey
    9 nights / 8 days
    £692.00
    • CLVW9
    • Helmsley to Filey
    • 9 / 8
    • 108 / 174
    • £692.00
    • Helmsley
    • Helmsley to Sutton Bank
      10 / 16

    • Sutton Bank to Osmotherley
      12 / 19

    • Osmotherley to Clay Bank Top
      11 / 18

    • Clay Bank Top to Roseberry Topping
      13 / 21

    • Roseberry Topping to Staithes
      19 / 31

    • Staithes to Robin Hoods Bay
      17 / 27

    • Robin Hoods Bay to Scarborough
      12 / 19

    • Scarborough to Filey
      11 / 18

    • Filey