Here's a round walk from Chinley Station via Cracken Edge (10k, approx. 2hrs)
This walk has a lot of steady climbing and descending, some very pleasant walking on level moorland paths, and a couple of steep bits both up and downhill. See the last page of this guide for a route map.
There is some walking on quiet rural roads, a section of farmland track and a good deal of firm moorland paths. Trainers or strong shoes are fine, walking boots a matter of choice. A walking pole is a good idea for keeping you steady in two locations if the weather has been wet. There is one stepped stile to be negotiated – the stile is safe and in good state repair. Compass bearings are given.