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Climb both of the area's best-known hills on a full circuit through Newton Wood, Great Ayton, Cliff Ridge Wood and the Cleveland Way. From the National Park car park at Newton-under-Roseberry, follow Roseberry Lane and the woodland bridleway to join the circuit. Walk around the lower woodland edge, visit Great Ayton village green, then retrace the field path to Cliff Ridge Wood. Continue by Aireyholme Lane and Ayton Banks to Captain Cook's Monument, cross Gribdale and follow the moorland trail to Roseberry Topping. Descend towards the folly and return through Newton Wood to the car park.
The route is about 14 km including the genuine car-park approach. It retains the complete Great Ayton visit and both summit climbs; the village path and parking approach are walked in both directions. Allow about five hours plus longer stops. This is a strenuous hill walk with steep stone paths, uneven steps, stiles and mud. Wear boots, carry layers and water, and choose clear, calm conditions. Keep well back from the steep drops around Roseberry Topping and stay on the walking paths.
Take care on the lanes, at road crossings and at the railway crossing near Great Ayton. Check that the railway is clear before crossing and follow its signs. Keep dogs on leads near livestock. Newton-under-Roseberry car park is charged and has public toilets; Great Ayton offers further facilities. Begin early enough to finish in daylight. Footpath restoration is taking place around Roseberry Topping: check current notices and follow signed closures or diversions.
Route geometry: © OpenStreetMap contributors, licensed under ODbL. https://www.openstreetmap.org/copyright
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