Jerry,
You posted something on this event before and I spent a little time looking for info on Quantrill and his followers during this period. Seems his men were pretty scatterred but it appears he and most of his men were in North Texas. At the same time, the Union reports in Missouri mention fighting bushwackers who claimed to be Quantrill's men or who they assumed to be Quantrill's men.

The Confederate Military authorities were struggling with what to do about him. They were afraid if they arrested him, his men would disband into numerous outlaw bands and terrorize North Texas (much worse than they were already doing). They wanted him to go back to Missouri and terrorize the Unionists.

As you well know, Quantrill's men were used to living off the land (and local residents), living in the saddle, and covering long distances, so it does not seem unusual that a fairly large band was up around Little Boggy and that at some time in the future joined up with the others to head north. Apparently groups of his men moved to and from their homes in Missouri as the urge struck them.

I'm aware of some references to the roads in this area and will see what I can dig up. Off the top of my head, Mrs. Caffrey lived on the road from Boggy Depot to Doaksville about "fifteen miles from the former place". I have assumed this road followed the Clear Boggy and then straight east to Doaksville. Caffrey's Crossroads were further east on this road -- east of the fork of Clear Boggy and Muddy Boggy. If I remember right, there was a road coming south from Johnson's Station on the Butterfield Road that intersected the Boggy Depot/Doaksville Road at Caffrey's Crossroads.

There were of course many minor roads and trails that don't show up on the old maps. Seems likely there was a road from around the Rocky Creek Ford that may have connected to the road south from Johnson's to Caffrey's Crossroads and then east. There was likely a road to Spencer Academy and then south.