Walking the Cleveland Way National Trail

About the Cleveland Way

The Cleveland Way National Trail is a 109-mile (175 Km) walking route from Helmsley to Filey in North Yorkshire. Check out our collection to help you stay on track while walking the Cleveland Way.

The Cleveland Way opened in 1969, and was the second National Trail in England and Wales (the first was the Pennine Way, opened in 1965). The trail offers the best of both worlds: the North York Moors and stunning coastal scenery, and is waymarked with the distinctive acorn symbol.

Walking the Cleveland Way follows a horseshoe-shaped route around the beautiful North York Moors National Park. Starting from the attractive market town of Helmsley, you will head across the heather moorland of the North York Moors before reaching the coast at Saltburn. From here the trail follows the dramatic North Yorkshire coastline to Filey, passing old fishing villages including Staithes, Runswick Bay and Robin Hood's Bay, and the lively coastal towns of Whitby and Scarborough.

There is a wealth of history and heritage to enjoy while walking the Cleveland Way including Helmsley Castle, Rievaulx Abbey, Mount Grace Priory, Guisborough Priory, Whitby Abbey and Scarborough Castle.

Check Out Our Cleveland Way Merchandise

Walking the Cleveland Way doesn’t have to be completed in one go to enjoy the best it has to offer. You can find maps and merchandise, along with books that include short walks on the Cleveland Way here:

CLEVELAND WAY COLLECTION

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How long does walking the Cleveland Way take, end to end?

The Official Cleveland Way Guidebook recommends a 10-day trip with between 9 and 14¾ miles each day. Sections can be shortened to shorten your journey, or if you would prefer a more casual walk, take a little longer to see more of the beautiful sites along the way.

Is walking the Cleveland Way hard?

Anyone who is reasonably fit can walk the Cleveland Way. The route is challenging in places, especially the coastal sections due to the steep steps and gradients but this adds to the overall experience. There are no stiles on the trail (the last stile on the Cleveland Way was removed in 2021). Whilst the route is well signed throughout, an up-to-date map such as this one is essential.

When walking the Cleveland Way, which direction should I go?

Most people walk the route from Helmsley through to Filey in a clockwise direction. This way you are likely to have the wind on your back for more of the time and most of our guidebooks are written this way. However, there is no right or wrong way, plenty of people enjoy walking it in the other direction.

If you are finding it hard to book accommodation you might want to walk the Trail in the less common direction. From Filey head north along the Yorkshire coast to Saltburn-by-the-Sea and then turn west and then south around the North York Moors National Park to Helmsley.

Who can enjoy walking the Cleveland Way National Trail?

The Cleveland Way is a long-distance National Trail primarily designed for walkers, although some short sections can be ridden or cycled.

Can I bring my dog while walking the Cleveland Way?

Your dog is welcome on the Cleveland Way. However, you will need to keep it under close control, we recommend a lead on the moorland stretches where there can be nesting birds and/or sheep. You may encounter cows with calves which can be very protective and aggressive towards dogs. If you experience any aggression near these animals, release your dog, do not try to pick it up. To make sure your dog stays happy while on your walk, why not bring one of our Dog Treat Bags.

What is the best time of year for walking the Cleveland Way?

The Cleveland Way can be walked right through the year, with each season offering something different. If you want to see the moorland heather of the North York Moors in bloom, then late August and September is the ideal time to walk the trail. Holiday destinations such as Whitby, Scarborough and Filey may be very busy during school holidays so it is wise to book accommodation in advance.

Can I buy Cleveland Way merchandise?

We sell a range of Cleveland Way merchandise including sew on badges, enamel badges, mugs and other merchandise. We also sell recycled Cleveland Way trail signs that have been removed from the trail. These are only available periodically, and always sell out fast – if you want one make sure you follow us on social media so you see when we get the signs in stock.