Well latecomer you seem to be getting plenty of advice and encouragement. Sadly we have just gone into Tier 3 and I am having to rack my brains, where to take Mrs BWW for our next walk, probably have to be Lee Brockhurst, which suits my diminishing stamina. Sifting through these thoughts the Cliffe, Hopton Hill, Nescliffe area has well signed rights of way with many other trails and a sufficiently well defined an area to explore at will without become disorientated, ideal to familiarize with a map. The car park off the Great Ness - Hopton Lane is quite spacious,
here. Hopefully the link will open up in the 1:25 scale OS map.
This enclosed area is particularly well connected to its surrounding countryside, so as familiarity develops it is a good area to plan and follow routes out of it. It will have another advantage as it is geographically well suited to be part of the framework of a number of linear routes, ideal training ground for time / distance a necessary skill in linear walking.
Also it is on sandstone, lighter feet in winter,
fortunately Wenlock is a bit out my Tier 3 area, terrible heavy clay under the Edge.