Cleveland Way


Trail Details
>   Prices from: £ 835.00 per person
>   Start / Finish: Helmsley / Filey
>   Distance: 109 miles (176 km)
>   Duration: 9 or 10 days according to choice
>   Availability: Any start date from March to October
>   Grading: Moderate
>   This National Trail is well way-marked with White Acorn signs

Cleveland Way Highlights

  • A superb walk of complete contrasts - wild moorlands & dramatic cliff tops
  • Spectacular walking on the North York Moors
  • Visit the remains of Rievaulx Abbey and 13th century Whitby Abbey
  • Visit the Captain Cook Monument in Whitby
  • Explore Robin Hood's Bay & its cliff-hanging cottages & smugglers’ hideouts
  • Enjoy a panoramic view of Staithes - one of England's most picturesque villages

The Cleveland Way follows a route of 110 miles through beautiful landscapes and ever-changing scenery. The contrast between the open heather-clad moorlands and the high coastal cliffs means that the trail is essentially two completely different walking experiences.

Beginning in the attractive market town of Helmsley, The Cleveland Way heads across the spectacular heather moorland of the North York Moors National Park before reaching the coast at Saltburn-by-the-Sea. From here it is a magnificent coastal walk along the dramatic and rugged North Yorkshire and Cleveland Heritage Coast to the seaside town of Filey, passing through beautiful, old fishing villages and lively coastal towns on the way.

Keen to find out more about walking the Cleveland Way? Check out our blog: Cleveland Way: 50 Years of Countryside & Coast.


During these unpredictable times we all want complete peace of mind when booking a holiday, so we're offering flexible postponement up to 3 weeks before the start of your trip at no expense to you. See our Book With Confidence page for more details.