The 7 mile walk linking Great Ayton with Captain Cook's Monument and Roseberry Topping is one of the most popular in the National Park. A longer route, adding two miles, is also described for those who want to explore further the easily accessible moorland with its spectacular views and historical connections. There's a climb of some 700ft up to the monument followed by two much shorter ascents.
Distance: 7 or 9 miles
Time: 4 to 5 hours
Grade: moderate
Conditions: well used paths and moorland tracks; best on a clear day
Refreshments: Great Ayton
OS Explorer Map OL26
Originally published: 24 August 2012
We start from Nicholas Dimbleby's statue of the young James Cook on the High Green (GR 564107). Walk past the Royal Oak and turn right along Station Road, signed to Little Ayton. In some 300 yards go straight ahead at a painted roundabout on a narrow lane which brings us to the pretty riverside hamlet. Turn left before the bridge over the Leven and follow the lane to Fletcher's Farm which has its own busy little stream and a coffee shop (open summer weekends).
Beyond the farm take the bridleway, left, which climbs gently to cross the Middlesbrough-Whitby railway. The way then continues to a tarred lane where go right on a path in trees high above an earlier hollow way to emerge in a field. Follow the fence on the left and turn sharp left with it. A welcome seat awaits those who wish to appreciate the views of the village below and the Cleveland Plain beyond.
Once revived you now enter Ayton Banks Wood, cross a forestry track and tackle the steepest part of the entire walk, emerging on to the moorland some 200 yards from the monument at 1064ft. It's time to draw breath and savour the inscription of 1827 to the achievements of one of our greatest explorers and his untimely death on Owhyee in 1779. The views are stunning too, especially along the line of the Cleveland Hills to the Pennines some 30 miles distant.
Our routes divide here. If you prefer the shorter 7 mile walk then, if you are facing the plaque, take the path to the left, the Cleveland Way, which crosses Easby Moor before descending through a large plantation to the car park at Gribdale Gate.Cross the road and climb the stepped path on the far side. At the top you enter Great Ayton Moor and follow a wall on the left for 1.5 miles. It still affords breathtaking views but is high enough to keep out the westerlies. It's easy, level walking and in a mile rejoins the longer route at Little Roseberry.
For the 9 mile walk follow the Cleveland Way in the opposite direction from the back of the mounument. There are brief glimpses of the Leven valley on the right as you cross the heather, but the path then descends through trees for a mile to the lane from Kildale into Lonsdale.
Bear left downhill into this remote green valley. You pass the 18th century Lonsdale Farm on the right and cross the beck which is a tributary of the Leven. Where the tarred lane turns sharp left go ahead on a rough track.
This once linked the Percy lands of Kildale with the Brus lands in Guisborough and, later, the lands of Guisborough Priory. It's a short, possibly muddy climb but at the top is the site of Percy Cross, mentioned in 1231, which marked the boundary of the two estates. Only the base of the cross remains today.
Here you also join Ernaldsti, one of the main  north-south crossings  from medieval times and named after Ernald de Percy, lord of Kildale. If you have an interest in prehistory then it's worthwhile diverting sharp right down the track for 300 yards to the remains of a tiny Iron Age settlement of 5 round, stone based huts, excavated in 1961-4 by Rowland Close.
Our walk follows Ernaldsti north as it climbs gently to the summit of Hutton Moor. After half a mile you pass a curious brick building, marked as a Lookout Post by one writer. It could hardly be in a better position for there are sweeping views of the coast from Hartlepool Bay to Huntcliff. Highcliff too is prominent ahead whilst if you look back the medieval track south is clearly visible as it rolls over the moorland ridges  on its way to Westerdale, Ralph Cross and Kirkbymoorside.
In another half mile we reach the edge of the scarp where Ernaldsti enters trees and drops steeply down on its way to Hutton Lowcross and Guisborough. Turn left here, following the Cleveland Way along the edge of the plantation. In about 400 yards bear left through a gate over open moorland to Little Roseberry to join the shorter walk.
Roseberry Topping is about half a mile distant with a gentle drop to a saddle before the sharp 300ft climb on a paved path to the summit at 1051ft. Again the views are outstanding with the sea, industrial Teesside and the Durham hills in the distance, and Great Ayton, Newton-under-Roseberry and Guisborough and its priory closer to hand.
Ignore the popular path down to Newton on the north side. Our descent is down the steep south side on a paved path, heading first for a pretty 18th century summer house visible below. It was built by Commodore Wilson of Ayton Hall.
Our path passes to the left of the building and continues across fields to Aireyholme Cottage, set in trees. Continue across the next field to yet another fine viewpoint overlooking Great Ayton and the Cleveland Plain. The path turns left over a stile and in a few paces enters Cliff Ridge Wood by a second stile.
It's now all downhill. In 250 yards you cross the main path running along the bottom of the wood and in a few more yards leave the trees. The well used path is now easy to follow across one field and over the railway. For the last half mile it is confined as a narrow right of way, punctuated by a series of cast iron kissing gates, the last of which is at the very edge of Newton Road (watch for the traffic). Turn left for High Green.