Cleveland Way Hiking Tours

This immersive trail is a quiet, enchanting slice of northern English moors and coastal life. The 11-day trip is graded easy to moderate. There are a few days where you are hiking approx. 15 miles daily, and it’s best to be prepared for multiple ascents and descents through rolling moorland and along imposing sea cliffs. A good head for heights is also recommended.

The Cleveland Way is perfect for:

• Nature enthusiasts eager to delve into diverse ecosystems, from some of the UK’s greatest moor hiking to clifftop walking with enchanting views of the North Sea shoreline.
• Folks new to multi-day hiking, who want to complete a route that's both enjoyable and a little bit challenging, passing Roseberry Topping 'Yorkshire's Matterhorn'.
• Self-guided hikers who enjoy the freedom and flexibility of getting from A to B (or inn to inn) at their own pace, and stopping where they wish along the way - maybe popping into Whitby Abbey of Dracula fame.
• Folks looking to get a small taste of England’s renowned Coast to Coast National Trail as well as sections of the new Kings Charles III Coast Path (a new route that follows the full coastline).
• Solo travelers looking for a safe and scenic route with opportunities to come across fellow hikers, including Coast to Coasters on the final leg of their long-distance hike, spending the night in Robin Hood's Bay.

Learn more about the delights of the Cleveland Way trail experience from journalist Ben Lerwill of The Times.

Macs Adventure has been specializing in self-guided hiking vacations across England since 2003. We offer:

Local Expertise: With team members based in England, we provide insider tips and recommendations for must-see attractions like Whitby Abbey and Rievaulx Abbey England.

Stress-Free Planning: Enjoy pre-booked accommodations, daily luggage transfers, and a detailed Cleveland Way route map in our user-friendly app.

Diverse Experiences: Discover England's countryside, connect with friendly locals, and explore iconic landmarks like Scarborough Castle England.

Handpicked Accommodations: Stay in small, family-run guesthouses and inns offering comfort and character.

Whether you’re a seasoned hiker or newer to long-distance hiking, our Cleveland Way walking vacation and other trips let you explore England’s national trails at your own pace, combining adventure with relaxation.

•    Where is Cleveland, England?
Cleveland is a historic area in northeastern England, home to a section of the Cleveland Way trail. It includes parts of the North York Moors National Park, the Cleveland Heritage Coast as well as segments of the Coast to Coast National Trail and the new King Charles III Coastal Path.

•    How long does it take to hike the Cleveland Way?
The full Cleveland Way trail is 109 miles and typically takes 9–11 days, depending on your pace and itinerary. 

•    How long is the Cleveland Way route?
The Cleveland Way route spans 109 miles, combining moorland trails and coastal paths.

•    When is the best time to walk the Cleveland Way?
The trail is most popular between April - Oct., with August and September offering spectacular views of blooming purple heather on the moors.

•    What do I need for navigation?
The Cleveland Way is well-waymarked, making navigation straightforward. Macs Adventure provides detailed route maps with app-based GPS navigation for added peace of mind.

•    Is there a connection between Robin Hood and Robin Hood’s Bay? 
Legend has it the town was named after rebel outlaw Robin Hood. After he fought off the French pirates who pillaged fishermen’s boats and villages along the coast and returned the stolen loot, the villagers named the town in his honor. Unfortunately, there is no concrete evidence that supports this local legend.

Enhance your Cleveland Way walking vacation with these unique experiences:

Robin Hood's Bay: Stroll along cobbled streets, explore sandy beaches, and learn about the village’s smuggling, sailing and fishing history. 

Wildlife Spotting: Witness grey seals and seabirds along the coastal cliffs and grouse and deer on the moors, immersing yourself in England’s natural beauty. The varied terrain is home to a plethora of bird species. 

Helmsley Brewery: Start your journey with a visit to this family-run brewery, known for its handcrafted Yorkshire beers. 

Explore the Cleveland Way with Macs Adventure and discover a side of England that blends rich history, stunning landscapes, and warm hospitality. Whether you’re tracing ancient paths or relaxing in seaside villages, every step of this trail offers an unforgettable experience.

Whitby Abbey: Explore the dramatic ruins of this iconic site, perched high on a cliff and famously featured in Bram Stoker’s Dracula.

Scarborough Castle: A medieval fortress overlooking the sea, offers breathtaking views and a glimpse into Yorkshire’s storied past.

Roseberry Topping: Known as ‘Yorkshire’s Matterhorn,’ this unique hill offers panoramic views of the Cleveland Hills and coastline.

Rievaulx Abbey: Visit the tranquil remains of this once-grand monastery, nestled in a wooded valley.