In reply to climb the peak:
> Win Hill looks like a good bet
Win Hill via Parkin Clough is some sort of a benchmark for sure. There are lots of circular routes you could devise to include a lot more ascent too, depending on how many miles you're looking to clock up. Taking in the summit of Lose Hill is probably the most obvious, but you could also visit the Eastern slopes of the Kinder plateau. (eg: up Jaggers Clough)
> as does walking up to Kinder from Snakes Pass
Aaargh. I can just about cope with "Peaks", but this is a step too far!
> heading up to Derwent Edge from Ladybower.
If you're up for the mileage you could link that in to the schlep up Win Hill by dropping down to cross the Ashop (and then the A57) at Haggwater Bridge, Rowlee Bridge or Alport Bridge and going up, over the ridge and down again to Fairholmes. (The climb up to Alport Castles from Alport Farm is another particularly good one.)
Also it's worth knowing that there's a path that leaves the back of the Heatherdene car park and goes directly uphill across access land to Bamford Edge. You can link that in to Derwent Edge by crossing Jarvis Clough and taking the track back down to Cutthroat Bridge.
If you're planning routes, it's worth looking at the Open Street Map and even the Strava Heat Map to spot some quite well trodden paths that you wouldn't find from looking at the OS map alone.
> I'll take a look at the more local walks and report back.
Cool, I'd be interested to hear how you get on.