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@eone
from hunter's bar roundabout you can go through endcliffe park on the bridleway until you get to the quiet lane, then up to redmires reservoir and there's another bridleway that goes to the bottom of stanage. then you'll probably have to take the road to castleton and over winnat's and pick up the pennine bridleway which goes up to glossop. not sure about an off road route in from glossop, have a look on an OS map.