Thanks Jeff,
I am tracking this route myself, I think he left portsmouth, taking the old dover rd (still exists), then following rt 108 thru rochester, rt 11 west to 153, farmington , milton, and the old kings road to Wolfeboro.
I believe these are the 'best pioneer roads' as shown in Document.
let me know if this helps anyone!
below a pic of the mansion in Portsmouth HH
