Cleveland Way Walk

The Route

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Start Point: Helmsley, North Yorkshire, YO62 5AB

Finish Point: Filey Brigg, North Yorkshire, YO14 9ET

Distance: Approximately 109 miles (175 kilometers)

Walk Description

Starting Point: Helmsley, North Yorkshire, YO62 5AB

Key Highlights:

  • Helmsley: A charming market town with a historic market square and the ruins of Helmsley Castle.
  • Rievaulx Abbey: Beautiful ruins of a former Cistercian monastery set in a wooded valley.
  • Sutton Bank: Offers spectacular views over the Vale of Mowbray, including the White Horse of Kilburn.
  • Roseberry Topping: An iconic hill with a distinctive shape, providing stunning views from the summit.
  • Whitby: A historic seaside town famous for its Abbey and connections to Bram Stoker's Dracula.
  • Robin Hood's Bay: A picturesque fishing village with steep streets and scenic views.
  • Scarborough: A bustling seaside resort with sandy beaches, a castle, and plenty of attractions.
  • Filey Brigg: The end point of the trail, known for its birdwatching opportunities and dramatic coastal views.

End Point: Filey Brigg, North Yorkshire, YO14 9ET

Practical Information

Distance: Approximately 109 miles (175 kilometers)

Difficulty: Moderate to challenging – the route includes some steep ascents and descents, particularly along the coastal sections.

Terrain: Mixed terrain including heather moorland, coastal cliffs, sandy beaches, and woodland paths. Some sections can be muddy and slippery, especially in wet conditions.


  • By Car: Parking is available at the start in Helmsley and the end in Filey. Intermediate points also have parking facilities.
  • Public Transport: Rail services connect to several points along the route including York, Thirsk, Middlesbrough, Whitby, Scarborough, and Filey. Regular bus services also operate along the trail.

Tips for Walkers

Footwear: Sturdy walking boots are essential due to the varied and sometimes challenging terrain.

Supplies: Bring sufficient water, snacks, and sun protection. Towns and villages along the route offer plenty of options for resupply and refreshments.

Navigation: The route is well-signposted with the National Trail acorn symbols, but carrying a detailed map (OS Explorer maps for the relevant areas) or a GPS device is highly recommended.

The Cleveland Way offers a spectacular long-distance walking experience, combining the heather moorland of the North York Moors with the stunning coastline of North Yorkshire.

Starting in Helmsley and finishing in Filey, this 109-mile route provides a diverse and memorable journey through some of England's most beautiful landscapes.

Whether you're drawn to the historical sites, the natural beauty, or the charming villages along the way, the Cleveland Way is a rewarding challenge for any walker!

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