Roseberry Topping and Captain Cook's Monument

Explore the North York Moors on the Roseberry Topping and Captain Cook's Monument hike - a 6.5 mile journey of moorland views, heritage, and adventure.

Length: 6.5 miles

Duration: 4 hours

Difficulty: Intermediate

From £35 per person

Discover Yorkshire's most breathtaking long-distance trails with Hike Yorkshire's expertly guided multi-day adventures. Our itineraries combine stunning landscapes, fascinating local history, and comfortable accommodation leaving you free to focus on the journey.

Ex- military guides

Educational hikes

Historical and folklore commentary throughout

Small groups

Do you need a guide?

Hike Yorkshire provides ex-military guides who are highly trained in navigation, first aid, fieldcraft, and fitness. Their local knowledge is invaluable in ensuring your day out is both educational and enjoyable.

Conditions on the hills can change quickly, so taking a well-drilled professional along is the best way to make sure everyone returns safe and happy.

Discover the dramatic scenery and historic charm of the North York Moors on the Roseberry Topping and Captain Cook's Monument hike.

This 6.5-mile trail takes walkers through rolling moorland, scenic valleys, and quaint villages before ascending Roseberry Topping, a striking hill resembling the Matterhorn, offering panoramic views across Cleveland and Teesside. Continue on to the Captain Cook Monument, commemorating the world-famous explorer, perched on a rugged hilltop.

This intermediate hike combines moderate climbs with rewarding viewpoints, making it ideal for walkers seeking a blend of natural beauty and history. Along the route, enjoy abundant wildlife, heather-filled moors, and insights into the area's geology and local legends from your guide. The combination of adventure, history, and stunning scenery makes this walk a must-do for North Yorkshire visitors.

Sights of Interest

Roseberry Topping – an iconic, sharply shaped hill offering wide views across the Cleveland Hills
Captain Cook's Monument – a prominent hilltop monument celebrating the explorer's local heritage
Newton Wood – peaceful woodland paths linking lower trails to open hillside
Cleveland Hills – rolling moorland scenery forming the northern edge of the North York Moors
Great Ayton – a traditional village closely associated with Captain Cook's early life

Why Choose Roseberry Topping?

A striking walk to one of Yorkshire's most recognisable hills, with panoramic views across the Cleveland Hills
A route rich in history, linking open moorland with the legacy of Captain Cook's early life
An achievable intermediate hike offering a rewarding challenge without committing to a full-day trek