Loads of options!
BigMassive route:
Start off up and over Chinley Churn, then along Roych Clough and Rushup Edge to Mam Nick. Then head for Hollin’s Cross and drop into the Edale valley near Nether Booth. Up to Hope Cross, then down the beast, over to Ladybower and haul yourself up to Stanage and head in to Sheffield that way.
You could extend that to Blacka too if you fancied.
Short cuts to that might be using Jacob’s to get into Edale, or missing out Ladybower and dropping off Hope Brink to Aston.
A totally different route would be to drop into Castleton/Hope from Hollin’s Cross. You could then either head up the valley, or go up Shatton moor and down that nice singletrack descent to Offerton Hall.
Massive climb up from there to Blacka/Stanage though…
I’ve not done that ride for a while. Might have to look in to it soon. One nice thing about it is that if you do bite off more than you can chew, it’s usually not too far to bail to a train station.