Great days out...the Cleveland Way

The Cleveland Way is a fantastic route for walking and in parts cycling and horse riding through the ever-changing scenery of the North York Moors National Park.

This section describes our suggested 'Top Ten' experiences for you to enjoy along the Trail.

From the attractive market town of Helmsley, across inspirational and often vibrant heather moorland, to the characterful coastline at Saltburn. From there it’s a visual feast along the dramatic North Yorkshire coastline, passing old fishing villages and lively coastal towns.

The trail covers a total of 109 miles, but of course you don’t have to do it all at once! There are fantastic days out to be enjoyed along its course, a selection of which are described below.

What are you waiting for? Go and explore!

Getting around

Information on public transport is available at

What to bring with you

We recommend downloading and printing a copy of our easy-to-follow walking maps, which are available for each 'Top Ten' destination along the Trail. You'll find links to download the walking maps on the pages listed below.

Suitable outdoor clothing and footwear are also recommended. A map of the area is useful but not essential (Ordnance Survey map number OL26 and OL27). You might like to bring a pair of binoculars for spotting wildlife. You could also purchase the new A-Z Adventure Atlas for the Cleveland Way available form National Trial shop.

Accommodation, food and drink

Information on staying and eating locally is available at

The Cleveland Way Top 10 Trail Experiences

Make a pilgrimage from Helmsley Castle to Rievaulx Abbey © Mike Kipling
Follow in the footsteps of Saint Aelred of Rievaulx, one of Yorkshire’s most famous abbots, on this historic walk from Helmsley Castle to Rievaulx Abbey. The route takes in magnificent woodland, the valley of Blackdale Howl and stunning views from the top of Jinny York Bank.

Enjoy a great view at Sutton Bank: day or night!
Sutton Bank, on the edge of the North York Moors National Park, provides spectacular views over the Vale of Mowbray. From here you can spot gliders soaring above, watch the weather roll in from the west, gaze at the starry night sky or enjoy a bike ride through beautiful woodland.

Scramble through the Wainstones © Mike Kipling
A more adventurous walk up Hasty Bank to the unique Wainstones will not disappoint. As the only part of the Cleveland Way where you need to use your hands for a very short scramble, the Wainstones present a small yet satisfying challenge.

Stride in the footsteps of Captain Cook and climb your first ‘mountain’ at Roseberry Topping © Mike Kipling
Grab your chance to ‘bag’ two iconic features of the Cleveland Way on this circular walk from Great Ayton around Roseberry Topping and the site of Captain Cook’s Monument.

Surf Boards © Elaine Haworth
Here, the Cleveland Way rises onto the cliff top at Saltburn with dramatic views across the sea. This part of the trail provides a few surprises, with three artworks to discover along the route.

Be the highest person on the East Coast of England at Boulby Cliff, Staithes
This is a walk that offers two extremes: the chance to be the highest and then the lowest person on the east coast of England!

Whitby Regatta fireworks © Colin Carter
Whitby, like Scarborough, offers a perfect seaside experience.

Learn about wildlife and heritage at Robin Hood’s Bay
Robin Hood’s Bay has a long and interesting history – from its spectacular geology, to its former role at the heart of the local fishing industry. Explore this iconic landscape with a Coast Alive Tracker Pack.

Mindful Meander - Ravenscar
Ravenscar is a quirky village built on spectacular cliffs. During Victorian times there were big plans for the village to rival Scarborough and Whitby, until the company responsible for its development became bankrupt.

Hayburn Wyke
Hayburn Wyke is a secluded cove between Scarborough and Whitby. With the beach and woodland to discover, this hidden gem is the perfect setting for a picnic or a day of exploration.