Win Green, Wiltshire
Win Green, National Trust land, is in Wiltshire but is just 4 miles east of Shaftesbury. Win Green is the highest point of the Cranborne Chase, and was a favourite area for King John to hunt, it retains an ox drove, one of the longest and most ancient routes in the country, linking Axminster in Devon with Ivinghoe Beacon in Buckinghamshire, and is linked to the Wessex Ridgeway. Win Green overlooks the Ferne Park estate, and is owned by billionaire Viscount Rothermere, Chairman of the Daily Mail. There is a small, free, car park, no facilities, lots of cow or sheep dung. It's absolutely stunning, take a kite, it gets nice and windy up there. Say hello to the HighPark Cattle™.
Rough paths but good views from car park area.