The Cleveland Way National Trail

Friday 16th August, 2019 by Host & Stay

2019 marks the 50th anniversary of the Cleveland Way! With heather clad moorland and incredible coastlines, it has everything you could want in a trail. In today’s blog, we’re taking you through the walk and showcasing what you can expect along the way…

Starting on the southern edge of the North York Moors National Park in Helmsley, the Cleveland Way journeys all the way to Filey on the east coast. As you journey through Yorkshire, you can expect beautiful views, vast moorland, castles, spa towns and quaint fishing villages.


The very starting point of the Cleveland Way is the charming market town and civil parish of Helmsley, in the Ryedale district of North Yorkshire. Here you’ll find history and character wrapped up in striking architecture, which includes 51 listed buildings. The town is packed with flair – from the Michelin-starred restaurants and a lively market square to the specialist boutiques and microbrewery.

From Helmsley, it’s a 62-mile jaunt to reach Saltburn-by-the-Sea. This walk is known as The Moorland Highlights as it has beautiful views across the North York Moors. You’ll walk from the edge of the North York Moors National Park and follow the Cleveland Hills to the coast.

The first place you’ll reach is Sutton Bank, which has a near vertical drop from top to bottom scaling around 140 metres high. Can you believe that the rocks that can be found here cover more than 60 million years of earth’s history? They vary from gritstone, clay, limestone, shale and mudstones. If you’d like more information on the Jurassic history of the Bank, you can visit The ‘Lime & Ice’ exhibition at the Sutton Bank National Park Centre.



From Sutton Bank, you’ll find Osmotherley which is a quaint village elevated at around 200m with wide views across the Yorkshire Dales. You’ll find the Cleveland Hills in the North and Hambleton Hills to the South. Originally developed back in the 1800s as an overnight stop, Osmotherley has pubs, cafes and a fish and chip shop today.


OSMOTHERLEY > SALTBURN (35 miles / 57 km)

The Cleveland Way dips down into Kildale next on its way over the Esk Valley. This is the most strenuous part of the trail, but the views are breath-taking over the coast to the North and the deep valleys to the South.

From Kildale, you’ll ascent to Captain Cook’s Monument, then the moorland ‘Matterhorn’ before reaching Roseberry Topping. Despite its imposing figure, Roseberry Topping stands at 320m which is less than a third of the size of Scafell Pike, which is England’s highest peak. From here, you can expect softer farmland, woodland and riverside track to the coast of Saltburn.

As a key part of the Cleveland Way, Saltburn plays host to a number of our luxury holiday homes. Find somewhere to stay:


Toll Bridge Cottage was once the gateway to Saltburn’s ‘Ha’penny Bridge’ and is perfect for large groups / Details: 4 bedrooms and sleeps 8 guests / Price: From £150 per night.

The Artists Pad provides a world of inspiration with art and literature / Details: 2 bedrooms and sleeps 4 guests / Price: From £100 per night.

Artsbank Apartment is newly renovated with beautiful interiors / Details: 2 bedrooms and sleeps 4 guests / Price: From £120 per night.

View all of our Saltburn holiday homes.


SALTBURN > STAITHES (9 miles / 15 km)

The next section of the walk is known as The Coastal Highlights as it showcases stunning views of the beaches and cliffs along the North Yorkshire Heritage Coast. From Saltburn, the Cleveland Way hugs the coastline through to the small fishing village of Staithes.

Once one of the largest fishing ports in the North East, Staithes today is a mixture of winding streets, charming mismatched cottages and surprising art exhibitions. You’ll find more of our holiday homes here, making it a perfect stop off on your way.

Harbour Cottage is a 17th Century property with 3 floors making it ideal for groups and families / Details: 2 bedrooms and sleeps 4 / Price: From £125 per night.

Cowbar View Cottage is a quirky holiday home dating back to 1723 / Details: 4 bedrooms and sleeps 6 / Price: From £125 per night.

View the rest of our Staithes properties.


STAITHES > WHITBY (12 miles / 20 km)

The route continues along the coastline to Runswick Bay which is a small village huddled at the northern end of the gorgeous sandy bay. The postcard perfect spot has soaring cliffs and a popular yacht club right on the beach. The dramatic coastal paths then lead onto Whitby.

In Whitby, you’ll find a lively seafront bursting with amusements, shops and restaurants. It boasts a stunning Blue Flag beach and the infamous gothic Whitby Abbey.

It’s no surprise that we have over 10 amazing holiday homes in Whitby. Take your pick:

View Point Apartment sits right on the Cleveland Way in Port Mulgrave and boasts stunning sea views / Details: 3 bedrooms and sleeps 5 / Price: From £110 per night.

Osborne House is a stunning holiday home with plenty of charm / Details: 3 bedrooms and sleeps 6 / Price: From £150 per night.

Elysium House is a modern house perfect for large groups / Details: 3 bedrooms and sleeps 6 / Price: From £130 per night.

Rock Pipit Apartment is a stylish and comfortable pad which is ideal for couples / Details: 1 bedroom and sleeps 2 / Price: From £75 per night.

The Gulls Nest is part of a former Sea Captains house which was originally built in 1708 / Property: 2 bedrooms and sleeps 4 / Price: From £100 per night.

Discover all of Whitby holiday homes.


WHITBY > SCARBOROUGH (24.5 miles / 40 km)

An easy cliff top walk separates Whitby and the picturesque Robin Hoods Bay. From Robin Hood’s Bay to Scarborough, the route has ever-changing scenery with views of the Flyingdales Moor to the West and the North Sea to the East. You’ll find some steep paths along this way, where the sea breaks through the cliff top walk.

Once you’ve arrived at the popular seaside town of Scarborough, you’ll be welcomed by the lively seafront and beautiful beach. Colourful chalets line the seafront and you’ll discover shops, restaurants and pubs in the centre.


SCARBOROUGH > FILEY (10 miles / 16 km)

On leaving Scarborough, you’ll make your way to the final cliff top trail where you’ll end your journey at Filey. Throughout the last stretch, you’ll notice the colourful South Cliff and the coastal cliff views continue from Cayton Bay right through to Filey.

At Filey, you’ll find a gentler pace of life. Edwardian architecture weaves throughout the town and Filey proudly retains its fishing heritage. The town is unique, quiet and beautiful.


We’ve finally made it! That was a tough journey but completely worth it. Will you be taking the challenge? Plan your North Yorkshire stay with us. 

Share this article

Find your perfect retreat


Newsletter Sign Up


Sign Up

Get updates and inspiration straight to your inbox