It's always nice to break up a long journey into chunks seperated by something interesting to do. For my Scottish trip, the first leg split the journey from Chester into four chunks by visiting three castles not too far off route.
First just outside Penrith is Brougham castle (wiki)
A couple of interesting reconstructions of its appearance.
Across the border to Caerlaverock, where unfortunately the Scots mist had arrived. An unusual triangular affair it was beseiged and taken by Edward the first
A surprising amount of accomodation was fitted inside
Craignethan was quite a contrast a sixteenth century artillery fortification, unfortunately the massive artillery rampart was demolished.
The caponiere in the ditch (far end) is quite unusual and the nearer (later) version was an attempt to improve the design
The gorge around three sides makes this castle quite imposing, although the modern woodland prevents a clear view.