Great Ayton to Roseberry Topping and Captain Cook's Monument
- David Swabey
- Jan 1
- 2 min read
Updated: Jan 2
This is a walk originally published as part of a series of 6 walks available as leaflets from the Tourist Information Centre (TIC) in Great Ayton. The TIC is now located in the Library, west of the High Green. Previously it was in the car park adjacent to the High Green.

Distance: 6 miles
Time: allow 3 hours.
Grade: strenuous
Conditions: this walk climbs two of the tallest hills on the North York Moors, but on well-used on footpaths and bridleways.
Refreshments: Great Ayton's High Green, Dikes Lane and Fletcher's (Woodhouse) Farm
From point 1 to point 2 on the map
Leave the High Green by Newton Road and in 100 yards take the footpath signed right through the first of a series of kissing gates. The Middlesbrough to Whitby railway line is crossed in 400 yards. Climb to Cliff Ridge Wood, after going straight ahead at the first crossing of paths in the trees.
On emerging from the wood go left and then right. Roseberry Topping is now in view and the path is straight and easy to follow. Keep to the left of Aireyholme Cottage and cross three fields before the final steep climb to the summit.
From point 2 to point 3 on the map
From the concrete trig point walk along the spine of the Topping, descend by a
steep paved path and climb again ahead to a gate on Little Roseberry on the edge of a conifer plantation. Here go right along the main route of the Cleveland Way, a fine one mile ridge walk which ends with a steep, stepped descent to Gribdale Gate. The Cleveland Way now climbs more gently through trees to the Monument.
From point 3 on the map to Great Ayton High Green
With your back to the plaque on the Monument go to the edge of the moor and turn right along it. The path soon descends steeply through trees. Take the right hand fork at a junction and after another sharp drop, cross a forest track to emerge from the woods into a field.
Turn right at the field corner and follow what develops into a deeply cut path for about 300 yards. It then becomes a tarred lane. After 50 yards go left down a gravel track, recross the railway and continue to Fletcher's (Woodhouse) Farm. From here follow the tarred lane into Little Ayton where turn right at the river bridge for a half mile walk back to the High Green.







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