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Some edge-of-Sheffield thoughts...
Cycling down Winnats is great fun and very scenic, but it does mean you miss Mam Nick, which is the road that turns left just before Winnats, and heads over into Edale. Mam Nick is probably the most famous climb in the Peaks around Sheffield, so you might want to divert purely for that reason, but then it is 'properly' done by climbing up from Edale. So from where you're coming from, I think cycling down Winnats will actually be nicer.
Then from Castleton to Hathersage you're following the main road, which is a good road to cycle as main roads go - it has a broad cycle lane for a long stretch, and is usually quite quiet and you can make good speed along it. But if you wanted a more scenic route, then after Hope turn north through the lanes to skirt around Hathersage and eventually join Ringinglow Road:
http://simonlikesmaps.appspot.com/share?key=ahBzfnNpbW9ubGlrZXNtYXBzchILEgVSb3V0ZRiAgICA8oiACgw
Then given you're heading to Nethedge you've made a good choice heading in down Ringinglow Road - a very pleasant way to arrive into Sheffield.
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sifriday
I was just wondering if any of you Peak Districtians could offer me some expert local advice? I'm putting together a LEJOG route (leaving in 10 days) and am going to stay with some friends in Sheffield. I wanted a nice route into and through the Peaks taking in Winnat Pass (purely because its the only one I've heard of). I've used a bit of @KT_Bee's route above, but the rest is just streetview and guess work. I'd love to hear if anyone would recommend any other bits of road as unmissable/climbs or passes preferrable to Winnats or routes into Sheffield preferable to that I have planned. Any advice or suggestions very gratefully received.
Cheers
http://www.mapmyride.com/routes/view/792761349