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. We have two Cleveland Way trips depending on how long you want your walking days to be - 11 Days & 10 Nights and 9 Days & 8 Nights. 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 

Kick off your adventure in the charming market town of Helmsley. Start with a visit to the stunning Helmsley Castle, where history comes alive through its impressive ruins. Wander through the Helmsley Walled Garden, a serene oasis perfect for a leisurely stroll or a picnic. Head to Helmsley Brewery. This family-run brewery has a mission ‘to make other people as passionate about handcrafted beer from the North Yorkshire Moors’ and offers tours and tastings. All beers contain Yorkshire Malts and at least one English hop, these then get combined with international hops from all around the world to create some flavoursome ales, such as ‘Yorkshire Legend’ or ‘Helmsley Honey’. And don’t miss out on a hearty meal at one of the local pubs—try the famous Yorkshire pudding! Get a good night's rest because tomorrow, the real adventure begins! 

Day 2 - Helmsley to Osmotherley (22 miles) 

Start your hike early and head towards Sutton Bank for exceptional views from the Sutton Bank National Park Centre. En route, why not take a detour to check out Rievaulx Abbey? This impressive site was once one of England’s most powerful monasteries and the first Cistercian abbey in the North of England. The museum tells you about the monks who called this abbey their home and the dramatic fall of the monastery.  

On your way to Osmotherley, don’t forget to stop by the iconic Kilburn White Horse, a giant hillside figure. The serene beauty of Lake Gormire offers a peaceful spot for reflection. End your day in the quaint village of Osmotherley, perfect for a restful night. 

Day 3 - Osmotherley to Clay Bank Top (11 miles) 

Today’s hike takes you through the remote moorlands and the tranquil Cod Beck Reservoir. This peaceful landscape is ideal for reflection and photography. Spot local wildlife and enjoy the sounds of nature. Arrive at Clay Bank Top, where you can unwind and marvel at the day’s accomplishments. There's nothing like a good meal and a cosy bed after a day's trek! 

Day 4 - Clay Bank Top to Roseberry Topping (7 miles) 

Adventure awaits as you trek towards Roseberry Topping, a distinctive hill with panoramic views. This shorter hike allows you to savour the smaller details of the landscape. Take your time, enjoy the wildflowers, and don’t forget to snap a selfie at the summit! The view is worth every step. You’ll also find Captain James Cook’s Monument here, one of the world’s most famous explorers who was born in Yorkshire in 1728. 

Day 5 - Roseberry Topping to Saltburn-by-the-Sea (12 miles) 

Descend from the heights of Roseberry Topping to the historic seaside town of Saltburn-by-the-Sea. Known for its Victorian pier and cliff tramway, Saltburn offers a delightful mix of natural beauty and historical charm. Take a leisurely walk along the pier, ride the Saltburn Cliff Tramway, and enjoy a well-deserved rest by the sea. 

Day 6 - Saltburn-by-the-Sea to Whitby (19 miles) 

Today's trek takes you along dramatic coastal cliffs, offering stunning ocean views. Pass through charming fishing villages like Staithes and Runswick Bay. End your day in Whitby, a bustling town famous for its abbey and Dracula connections. Treat yourself to some fresh fish and chips—you've earned it! Explore the ancient ruins of Whitby Abbey, the inspiration for Bram Stoker’s gothic tale of ‘Dracula’. 

Day 7 - Whitby to Scarborough (20 miles) 

Start your day by exploring the bustling old town of Whitby and browse local stores selling jewellery and trinkets made from the iconic Whitby jet – a semi-precious organic gemstone. 

As you head towards Scarborough along a stretch of coastal and inland beauty you’ll pass through Robin Hood’s Bay. Weave through the narrow-cobbled streets of this old fishing village and enjoy and take a tea break in one of the charming cafes.  

With the North Sea on your left and rainbow chalets on your right, Scarborough provides a cheery welcome. Visit Scarborough Castle and step into 3000 years of history - it has seen some of England’s most defining battles! Grab some fish and chips on the beautiful South Bay Beach and wander through the lush Peasholm Park.  
 

Day 8 - Scarborough to Filey (12 miles) 

Conclude your epic hike with a leisurely stroll along the cliff tops to Filey. This final leg of the journey offers stunning views and a sense of accomplishment as you reach the finish line in the charming town of Filey. Celebrate your achievement with a well-deserved rest and perhaps a celebratory drink at one of the local pubs. Enjoy the tranquility of Filey Brigg and take a moment to reflect on your incredible adventure.