Captain Cooke's Monument and Little Roseberry

Route Overview & Local Insights

This 9.9km loop from Great Ayton offers a quintessential North York Moors running experience, blending fast-paced village lanes with rugged, technical upland trails. With an ascent of 286m, the climb up to Captain Cook’s Monument is steady but demanding, technical enough to engage your stabilizing muscles while rewarding the effort with staggering panoramic views. From the monument, the ridge line over to Little Roseberry is a highlight for trail runners, providing a mix of peat, heather-lined singletrack, and undulating terrain that tests your footwork before a fast, sweeping descent back into the valley.

Rich in maritime and geological history, this area is the childhood home of the famous explorer James Cook, and the towering 1827 obelisk atop Ease Hill serves as a permanent landmark for runners and hikers alike. As you traverse toward Little Roseberry—the smaller, often overlooked sibling of the iconic Roseberry Topping—you are running through an ancient landscape shaped by alum mining and ironstone industries. On a clear day, the "Cleveland Hills" provide a dramatic backdrop that has inspired generations of fell runners and adventurers traversing the nearby Cleveland Way.