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, giving the walker panoramic views over the Cleveland Hills and the rest of the National Park. 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.
Click here to read about our colleague Lynne’s walk along the Cleveland Way.
Our Holidays
We offer 3 holidays 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, all of 5 days walking, covering the moorland section, the coastal section, and finally a bit of both.
When choosing your route, please bear in mind that the actual distance walked on any day may sometimes vary by up to 2 miles/3 km from the quoted distances, depending on the exact location of your accommodation. The mileages shown are typical door to door distances for each day.
The Whole Cleveland Way Path
Helmsley to Filey 107 miles/172 km
We offer 3 holidays covering the whole route. The longer the holiday, the shorter the distance you have to walk each day.
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 | $984 - $1185 | Full Info Book |
| CL10 | 9 days walking (10 nights) | 12 miles/19 km | $1180 - $1438 | Full Info Book |
| CL12 | 11 days walking (12 nights) | 10 miles/16 km | $1363 - $1678 | 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 | $750 - $893 | Full Info Book |
| CLM6D | 5 days walking (6 nights) | 12 miles/19 km | $891 - $1034 | Full Info Book |
Cleveland Way: The Coastal Highlights
Saltburn-By-The-Sea to Filey 52 miles/84 km
The Beaches and Cliffs section of the Cleveland Way taking in the dramatic North Yorkshire Heritage Coast.
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 | |
|---|---|---|---|---|
| CLC6 | 5 days walking (6 nights) | 10 miles/16 km | $750 - $893 | 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. Your dog can enjoy this route too. Just select the code ending D if you would like to book the dog-friendly option.
| Code | Length | Average per day | Price range | |
|---|---|---|---|---|
| CLJ6 | 5 days walking (6 nights) | 12 miles/19 km | $750 - $893 | Full Info Book |
| CLJ6D | 5 days walking (6 nights) | 12 miles/19 km | $891 - $1034 | Full Info Book |