Adventure Awaits, Exploring the Cleveland Way on Foot

Discover the North York Moors: A Self-Guided Hiking Adventure from Helmsley to Filey 

The Cleveland Way is a picturesque 109-mile (176 km) National Trail that winds through the diverse landscapes of the North York Moors, England. From the dramatic cliffs along the North Sea coast to the enchanting heather-clad North York Moors, this trail offers an immersive experience for every nature enthusiast, solo traveller, and adventure seeker. 

 
The Route 
 
The Cleveland Way starts in the quaint market town of Helmsley and ends in the coastal town of Filey. The route is divided into manageable sections that showcase a remarkable variety of scenery—rolling moorland, charming villages, ancient castles, and magnificent coastal views. 
 

Distance and Duration 

The full trail spans 109 miles and typically takes 9 days to complete, with an average daily distance of around 12 miles. However, the duration can be adjusted based on your pace and preferences. 

Difficulty and Terrain 

The Cleveland Way is part of our Classic Route trip types and is considered a moderate trail. While the coastal sections involve some steep ascents and descents, the inland sections across the moors are more gently rolling. The trail is well-marked and maintained, making it accessible to hikers with a reasonable level of fitness. 

Suitability 

This trail is perfect for: 

• Self-guided hiking enthusiasts who enjoy the freedom and flexibility of getting from A to B under at their own pace. 
• Solo travellers looking for a safe and scenic route with plenty of opportunities to meet fellow hikers. 
• Nature enthusiasts eager to explore diverse ecosystems, from moorlands to coastal cliffs. 
• Hiking newbies who want to complete a route that's both challenging and enjoyable. 

Suitability for Solo Travellers 

Solo travellers will find the Cleveland Way both safe and exhilarating. The trail passes through several villages and towns, offering plenty of opportunities to socialise and restock supplies. Plus, the warmth and friendliness of the locals are always a comfort. 

Suitability for Senior Travellers 

Senior travellers with a moderate level of fitness will find the trail manageable and rewarding. The availability of various accommodation options ensures comfort at the end of each day.

What to Expect on the Hike 

Things to Do and See Along the Hike 

Each section of the Cleveland Way has its unique charm: 

Day 1 - Arrive in Helmsley 

Your adventure starts in the market town of Helmsley, where picturesque old shops cluster around the market square. Visit Helmsley Castle, where 900 years of history come alive through its impressive ruins, then wander through Helmsley Walled Garden – a peaceful five-acre plot that's perfect for a leisurely stroll. If you fancy something hoppier, Helmsley Brewery is a family-run operation on a mission "to make other people as passionate about handcrafted beer from the North Yorkshire Moors" as they are. Every beer uses Yorkshire malts and at least one English hop, combined with international varieties to create ales like Yorkshire Legend and Helmsley Honey. Round off the evening with a hearty meal at one of the local pubs – this is Yorkshire pudding country, after all. Get a good night's rest. Tomorrow, the walking begins.

Day 2 – Helmsley to Kilburn (10.5 miles / 16.5 km)

The first highlight comes early. Rievaulx Abbey sits in the wooded valley of the River Rye, half a mile off the path and well worth the detour. Once one of England's most powerful monasteries and the first Cistercian abbey in the North of England, its museum tells the story of the monks who lived here and the dramatic fall of the monastery. From there the path climbs to Sutton Bank, where the view across the Vale of York was famously described by James Herriot as the finest in England. Look out for Lake Gormire glinting below the escarpment – a peaceful spot formed in the last Ice Age, with no river flowing in or out. Follow the path south past the Kilburn White Horse, a giant limestone figure cut into the hillside in 1857, before dropping down to your overnight stop in the village of Kilburn.

Day 3 – Kilburn to Osmotherley (15 miles / 23.5 km)

Retrace your steps up to Sutton Bank and turn north along the escarpment. There are some hill climbs to tackle today, but the views are worth the effort as you follow the old drovers' road towards Black Hambleton – a route once walked by cattle dealers moving their herds between Scotland and the markets of the south. The day ends in Osmotherley, a quaint village of stone cottages, old pubs, shops and cafes. An ideal spot for a well-earned pint.

Day 4 – Osmotherley to Clay Bank Top (11.5 miles / 18 km)

Shortly after leaving Osmotherley, you'll pass Cod Beck Reservoir, a tranquil stretch of water fringed by woodland and moor – a lovely spot for photos before the real work begins. This is the most strenuous day of the walk, a giant rollercoaster over the Cleveland Hills with a succession of ascents and descents. The reward is far-reaching views across heather-clad moorland and the deep valleys to the south. At the Clay Bank Top junction, a transfer takes you to your accommodation in the surrounding area. There's nothing like a good meal and a comfy bed after a day like this one.

Day 5 – Clay Bank Top to Captain Cook's Monument (12 miles / 19 km)

After a transfer back to Clay Bank Top, a steep climb leads to Round Hill on Urra Moor – at 454m, the highest point of the whole walk. The moorland walking up here is fantastic, though watch your footing as some paths can be boggy. As the path descends towards Kildale, you'll pass ancient burial mounds and boundary stones, quiet reminders of the people who crossed these moors long before you. From Kildale, climb Easby Moor to Captain Cook's Monument, built in memory of the famous circumnavigator who was born in Yorkshire in 1728 and grew up in nearby Great Ayton. A short transfer then takes you to your overnight accommodation in Great Ayton or Newton under Roseberry.

Day 6 – Captain Cook's Monument to Saltburn-by-the-Sea (11.5 miles / 18.5 km)

A morning transfer returns you to the Captain Cook's Monument car park, and today the moors gradually give way to the sea. Keep an eye out for Roseberry Topping, the distinctive half-dome hill sometimes called Yorkshire's Matterhorn – its summit makes a rewarding detour with panoramic views over the moors and out to the coast. The path then leads through farmland, woodland and along a riverside stretch into Saltburn-by-the-Sea. This Victorian seaside town is known for its pier – the last remaining pleasure pier in Yorkshire – and its water-balanced cliff tramway, which has been carrying people between town and beach since 1884. Take a ride, stroll the pier, and enjoy a well-deserved rest by the sea.

Day 7 – Saltburn to Runswick Bay (12.5 miles / 20 km)

From Saltburn, the walk hugs the coastline all the way to Filey. Climb Hunt Cliff and follow dramatic clifftop sections past Rock Cliff, the highest point on England's east coast. The path then descends into Staithes, a pretty fishing village where you'll spot a fleet of cobles – flat-hulled fishing boats whose design dates back to the Vikings. Continue along the cliffs to Runswick Bay, a picture-postcard village tumbling down to a mile of sheltered, sandy beach. One of the loveliest overnight stops on the whole route.

Day 8 – Runswick Bay to Robin Hood's Bay (15 miles / 25 km)

More dramatic coastal paths lead you to Whitby, a town steeped in history with narrow streets and a picturesque harbour. High above the town stand the ruins of Whitby Abbey, the inspiration for Bram Stoker's gothic tale of Dracula. Browse the old town's shops selling jewellery made from Whitby jet – a semi-precious gemstone found along this coastline – and treat yourself to fish and chips. You've earned it! Beyond Whitby, apart from a few steep inclines, the walking is gentler. Grassy cliff paths cut above old smugglers' coves lead to the iconic village of Robin Hood's Bay, where narrow cobbled streets wind down to the sea. This is where Wainwright's Coast to Coast ends, so expect plenty of fellow walkers in the pubs to swap stories with.

Day 9 – Robin Hood's Bay to Scarborough (15.5 miles / 25.2 km)

Continue along the coast towards the Victorian resort of Scarborough, following grassy tracks over a few steep gradients including the climb to Ravenscar – once earmarked to become a resort town itself, though the plans never quite came off. As you near Scarborough, busy beaches and traditional seaside entertainment offer a cheerful contrast to the untouched villages you've passed so far. Visit Scarborough Castle and step into 3,000 years of history, grab fish and chips on South Bay Beach, or wander through the oriental-themed gardens of Peasholm Park.

Day 10 – Scarborough to Filey (8.5 miles / 13.5 km)

Your final day is a gentler one – a stroll along clifftop tracks with a few ups and downs, and plenty of chances to look back at the colourful cliffs of South Bay. The Cleveland Way ends at Filey Brigg, a narrow rocky peninsula jutting into the North Sea. Take a moment here to reflect on 110 miles of moorland and coast before your transfer back to Scarborough, where a celebratory drink is very much in order.

Day 11 – Onward Travel

Enjoy one last hearty Yorkshire breakfast before making your way to the station for your onward journey – and start plotting the next adventure.