UKH

Planning to walk from peniston near Sheffield to Chester. Anyone done a similar multi day expedition or covered any of the terrain I will be passing. All thoughts, suggestions and advice welcome.

If you are serious you might want to include the mid Cheshire ridge from Beeston Castle to Bickerton hill via Rawhead.

The shortest and easiest way to start would be to follow the Trans Pennine Trail to Dunford Bridge and then up Windle Edge in to Longdendale, very little of the A628 road is walkable due to the lack of footpaths and heavy traffic. The TPT can be followed to Hadfield, or you could follow the edges north of the road from Crowden, or various options are possible over Bleaklow via Near Black Clough, a scramble up Wilboar Clough or head south on the Pennine Way from Torside. it all depends on how wild and arduous a route you're looking for.

Nb. it's Penistone

How about over the moor to Edale, over to Wildboarclough then Macclesfield. Cross country to Middlewich then pick up the Dee near Anderson boat lift?