Roseberry Topping from Guisborough

The route

Roseberry Topping's shape is the whole story here - a small, sharply pointed hill with one side collapsed into a near-vertical cliff, the result of old ironstone and alum workings undermining the summit in the 1900s. It's often called Yorkshire's Matterhorn, which oversells the scale but not the drama of the silhouette against the flat Tees lowlands. This route climbs from Guisborough through forest before crossing open moor to the final approach.

The summit

The last stretch to the top is steep and rocky, more of a scramble than a run, and worth taking slowly, especially descending in wet conditions when the worn rock gets genuinely slippery. From the top, the view stretches from the North Sea to the Cleveland Hills, and locally the hill has a real claim to fame: a young James Cook, later the famous explorer, is said to have climbed it often as a boy from nearby Great Ayton village.

Why it works

At 17.3km with 334m of ascent, this route uses the approach from Guisborough rather than the shorter, busier path from Newton under Roseberry, giving you more genuine trail and forest running before the short, sharp finish. It's a good moderate day with a properly distinctive summit as the payoff.

Getting there

The Newton under Roseberry car park is the more popular start if you want the shortest route to the top, but starting from Guisborough gives a longer, quieter approach through Guisborough Woods, with the added bonus of passing the ruins of Guisborough Priory on the way out of town. Great Ayton, a few kilometres beyond Newton under Roseberry, makes a good extension if you want to add more distance and see more of the wider Cook family connections to this quiet stretch of North Yorkshire countryside.