I think there are nicer places to base yourself than Glossop if you’re looking for road riding, walking and easy access to Manchester. Although it has many strengths – and location is one of them – it’s not a quaint or pretty tourist town.
One thing I will point out is that Glossop is surrounded by some pretty big hills that aren’t all traversed by roads. You can get a great road ride in with some big climbs and stunning views, but much of it is likely to be on A roads.
There’s potential to have a great weekend if what if offers fits what you’re after, but your requirements are a bit vague to give you the full seal of approval.