Cleveland Way

The Cleveland Way, established in 1969, is both an interesting and 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.