Cleveland Way

The Cleveland Way, established in 1969, is both an interesting and a beautiful path. It stretches for over 100 miles from Helmsley, on the southern edge of the North York Moors National Park, to Filey on the east coast.

The way passes through two very distinct types of landscape. From Helmsley to Saltburn-by-the-Sea, it traverses classic moorland scenery, through forests and along escarpments, rewarding you with panoramic views over the Cleveland Hills and the rest of the National Park.

In the beautiful Rye Valley you can marvel at the ruins of Helmsley Castle and the medieval Rievaulx Abbey. Ahead of Sutton Bank take time to view the magnificent Kilburn White Horse. Roseberry Topping, often referred to as the Yorkshire Matterhorn is a wonderful viewpoint. Despite its relatively low height of 1000 feet it is a tremendous place from which to survey the land around you.

The other half of the route, from Saltburn-by-the-Sea to Filey, follows a dramatic coastline and runs along the top of some of the highest sea cliffs in the country. Whitby, with its fine harbour, fossil filled cliffs and connections with Bram Stoker’s Dracula is a favourite of many and a visit to the imposing remains of Whitby Abbey is a must. Robin Hood’s Bay, the end point of the Coast to Coast and the seaside towns of Scarborough and Filey complete your coastal journey.

The combination of wild moorland and dramatic coastline make the Cleveland Way an incredibly varied, thoroughly enjoyable and hugely rewarding experience.

Our Holidays

We have 4 holidays on the Cleveland Way. We offer 3 itineraries over the entire length of the route, from 7 to 11 days walking, depending on how far you want to walk each day, and how much time you want to relax and soak up the views! We have 3 shorter breaks, with mainly 5 days walking, covering the moorland section, the coastal section, and finally a bit of both. Each of the holidays have dog-friendly options.

Please bear in mind that the distances each day are trail distances only. They do not take into account walking to your accommodation. On some days the accommodation might be on or close to the trail but on other days you may need to walk one or two miles to get to your overnight stop.

The Whole Cleveland Way Path

Helmsley to Filey 111 miles/179 km

We offer 3 different itineraries covering the whole route. The longer the itinerary, the shorter the distance you have to walk each day. Our 10 night itinerary can also be booked with dog-friendly accommodation. Please select the code ending D if you would like to bring your dog with you.

Please note that many of our accommodation providers in Scarborough and Filey now operate a minimum two night policy, therefore it is likely you will spend the final two nights of your holiday in the same location, either Scarborough or Filey, with a transfer between.

Code Length Average per day Price range
CL8 7 days walking (8 nights) 15 miles/24 km £725 - £864 Full Info Book
CL10 9 days walking (10 nights) 12 miles/19 km £890 - £1068 Full Info Book
CL10D 9 days walking (10 nights) 12 miles/19 km £1047 - £1225 Full Info Book
CL12 11 days walking (12 nights) 10 miles/16 km £1056 - £1274 Full Info Book

Cleveland Way: The Moorland Highlights

Helmsley to Saltburn-By-The-Sea 60 miles/97 km

The Moorland and Meadows section of the Clevelend Way across the beautiful North York Moors. This holiday can also be booked with dog-friendly accommodation. Please select the code ending D if you would like to bring your dog with you.

Code Length Average per day Price range
CLM6 5 days walking (6 nights) 12 miles/19 km £568 - £667 Full Info Book
CLM6D 5 days walking (6 nights) 12 miles/19 km £620 - £719 Full Info Book

Cleveland Way: The Coastal Highlights

Saltburn-By-The-Sea to Filey 51 miles/82 km

The Beaches and Cliffs section of the Cleveland Way taking in the dramatic North Yorkshire Heritage Coast. This holiday can also be booked with dog-friendly accommodation. Please select the 5 night itinerary with the code ending D if you would like to bring your dog with you.

Please note that many of our accommodation providers in Scarborough and Filey now operate a minimum two night policy, therefore it is likely you will spend the final two nights of your holiday in the same location, either Scarborough or Filey, with a transfer between.

Code Length Average per day Price range
CLC5D 4 days walking (5 nights) 13 miles/21 km £589 - £668 Full Info Book
CLC6 5 days walking (6 nights) 10 miles/16 km £568 - £667 Full Info Book

Cleveland Way: The Combined Highlights

Osmotherley to Robin Hood's Bay 62 miles/100 km

The Moorland and Coast section of the Cleveland Way across the northern end of the Moors and down the North Yorkshire Heritage Coast. This holiday can also be booked with dog-friendly accommodation. Please select the code ending D if you would like to bring your dog with you.

Code Length Average per day Price range
CLJ6 5 days walking (6 nights) 12 miles/19 km £568 - £667 Full Info Book
CLJ6D 5 days walking (6 nights) 12 miles/19 km £620 - £719 Full Info Book

Client Feedback

Couldn’t fault anything. Luggage was waiting for us at every stop. The information provided could not be better. Contact with the company has been exemplary. Well done from a very satisfied customer!

Cleveland Way, May 2021
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Everything worked! We had a great week.

Cleveland Way, September 2019
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