I would get the relevant 1:50,000 OS maps - Landranger - then you can see where the route would take you and work out alternatives
Either borrow them from your library, or this is a good & cheap supplier -
www.dash4it.co.ukA couple of years ago I did a walk which takes in much of what you might want to do. I started at Marple, SE of Stockport, then followed the canal up through Hyde, Ashton-under-Lyne to Mossley then onto the Pennine Way
I stopped at Hebden Bridge, but you could go on to join the Leeds & Liverpool canal at East Marton, then on to Leeds, but as ZigZag suggested you might be able to cut the corner and head off to Leeds sooner - that's what the map's for. On the other hand, canal walking makes the navigation easy
I have also walked the L &L canal in that area, around the south Pennines/Skipton
Canal walking is simple enough - flat, good path, fairly direct compared to some footpaths, and avoids roads. They go through varied scenery - rural, urban, and industrial (that is, after all, why they were built); it's easy enough to come off them into towns & villages for shopping or accommodation, or if you decide to have a rest and catch a bus
And the PW is well served with food & accommodation. In fact for that whole route you will be in easy distance of pubs, towns, & villages
You asked about groups. I am in
www.backpackersclub.co.ukAs the name implies we go backpacking & camping, but sometimes for day walks. The Cheshire branch is quite keen & active. You could ask if they have anything planned in the near future
Or you could inqire about your local Ramblers, formerly called The Ramblers Association. They are pleasant enough and easygoing
Oh, I've just had a thought (I do that sometimes!) For walking north , instead of the Pennine Way, have a look at The Pennine Bridleway. This is intended to be used by horse riders & cyclists as well as walkers, which means it's a bit easier - gentler slopes and better surface