Top Experiences Cleveland Way

Top Experiences Along the Cleveland Way

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 traveler, and adventure seeker.

Cleveland Way way marker with a cow

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 & 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 & Terrain

The Cleveland Way is part of our Classic Routes trip type 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.

Purple heather on the North York Moors

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 travelers 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 Travelers

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

Suitability for Senior Travelers

Senior travelers with a moderate level of fitness will find the trail manageable and rewarding. The daily distances can be adjusted, and 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. 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.

Rievaulx Abbey

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 Center. 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 cozy bed after a day's trek!

Cleveland Way

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 savor 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.

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 Whitby Abbey and take a spooky Dracula tour.

Whitby abbey

Day 7 - Whitby to Scarborough (20 miles)

Start your day by exploring the bustling town of Whitby before heading towards Scarborough. This stretch offers a mix of coastal and inland beauty. Visit Scarborough Castle for a dose of history and enjoy the lively atmosphere of this popular resort town. Plenty of amenities and attractions await, from the beautiful South Bay Beach to 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.

Scarborough south bay

Places to Eat Along the Hike

From traditional pubs to quaint tearooms, here are our top dining recommendations:

Helmsley: Dating back to the 15th century, The Black Swan is a medley of Elizabethan, Tudor and Georgian architecture and offers hearty meals and a cozy atmosphere.
Osmotherley: The Golden Lion Inn is perfect for a well-deserved pint and some classic British fare in a comfy and cozy setting.
Clay Bank Top: While there aren't any eateries nearby, depending on where your accommodation is, there are a couple of options. If you're staying in the nearby Great Broughton, The Bay Horse is a great choice, offering a mix of traditional and contemporary food. Or if you're staying in Great Ayton, perched on the banks of the River Leven is The Bucks, which serves classic, hearty pub grub.
Newton-Under-Roseberry: The King's Head Inn has a menu brimming with seasonal pub dishes as well as moreish stone-baked pizzas.
Saltburn-by-the-Sea: The Seaview Restaurant takes humble coastal ingredients and elevates them to delicious heights accompanied by stunning views.
Whitby: You can't visit Whitby without stopping by Magpie Café -renowned for its fish and chips and seafood dishes.
Scarborough: A hotspot among the locals, Embers offers seasonal menus showcasing the best locally sourced Yorkshire ingredients.

Battered fish, chips and peas

Accommodation Types and Comfort

Accommodation options along the Cleveland Way range from charming B&Bs and guesthouses to comfortable inns and hotels. Most places provide breakfast to fuel your day’s adventure, and many offer packed lunches or evening meals.

Getting to the Start of the Hike

Helmsley, the starting point of the Cleveland Way, is accessible by bus from York or Thirsk. Regular train services connect these towns to major cities like London and Edinburgh, making it easy to start your adventure.

The Best Time of Year to Hike

The best time to hike the Cleveland Way is from late spring to early autumn (May to September). During these months, the weather is generally mild, and the heather on the moors is in full bloom, creating stunning purple landscapes. However, always be prepared for the unpredictable British weather!

Exploring the Cleveland Way is a rewarding experience that combines natural beauty, historical sites, and warm hospitality. Whether you’re a seasoned hiker or a beginner, this trail offers something for everyone.

For those seeking more points of interest, shorter distances per day, and a longer hiking trip, our Cleveland Way 11-day, 10-night itinerary is perfect. Wander around historic Helmsley, visit the Kilburn White Horse, and explore the stunning coastal paths of Runswick Bay and Robin Hood's Bay.

Ready to take the first step of your adventure? Book a call with one of our adventure specialists today to refine your itinerary and ensure you make the most of your Cleveland Way experience. Happy hiking!