Personally I would go up the Caldon as long as you don't mind not seeing any other boats moving as it is generally very quite. A couple of nice pubs up there, plus a staircase although not as daunting as the one you remember from Chester.
If you made good time down to Harecastle you could always keep going and do the Four Counties ring, that is how we ended up doing the Four Counties the first time. The plan was a short out and back but we so underestimated how far we would go each day that after the second day it made sense to carry on round the ring.