The two dicey legs that I see are the Providence-Hartford and Albany-Montpelier ones. If I add up my estimates for driving it I get:
PVD-Providence: 0.5 hours
Providence-Hartford: 1.5 hours
Hartford- Albany: 2 hours
Albany-Montpelier: 3 hours (less if Lake Champlain is still frozen over and you can drive across it)
Montpelier-Concord: 2 hours
Concord-Boston: 2 hours
Boston-PVD: 2 hours
I don't like the looks of it. Maybe if you had someone to switch driving with and a bunch of Depends.... If you do it counter-clockwise, you can decide @Montpelier to skip Albany and come in nice and safe.