In reply to MikeMarcus:
Check out Castle Naze near Chapel en le Frith, Hobson Moor Quarry is easily doable with a train to Stalybridge then a bus or bike to the crag. Wimberry isn't too far from Greenfield, especially the bouldering.
Stanage isn't too far from Hathersage, and Frogatt isn't to far from Grindleford, but being over in the east they're probably best left for a weekend.
Maybe worth checking out some of the quarries to the north in Lancashire too.