Race wise would certainly recommend the Totley AC series -
http://www.totleyac.org.uk/
Don't think the 2010 dates are on their website yet but the first three (Tigger Tor, Tigers Todger and Totley Moor) all on the FRA calender.
Others close to Sheffield and public transport would include Burbage Skyline, Hathersage Gala, Stanage Struggle, Bamford Carnival, Wolf's Pit for starters.
Stanage Struggle route would make another good 6 mile training run from hathersage -http://www.fbrc.co.uk/Struggle%20map.htm