Can't help on the route through VT, but I will suggest that if you can, plan your travel to avoid rush hours in the major cities. Once you hit Portsmouth you can go either north or south, but if you are choosing south to MA I might stay on 90, depending on where in MA you want to go. The Boston area has so much history so if that's your main focus I'd go there. If you want a beautiful national park, head up to Acadia in ME. How much time do you have? You can make the Boston area in a day-Maine would be more comfortable in two days. However, if you are leaving on Thursday p.m. you can drive a few hours and then stop somewhere along the way. That gives you two options for the next day: leave very early in the a.m. to get through the main cities OR wait until a little later on and go through them after rush hour.