if You can afford a motel for every night of your ride then that would be reasonable to try. Motel to maintain your wet clothes and to rewarm your body. I would skip the camping for this time. It will lighten your load tremendously and that will avail extra space in your bags for warm clothes, for heavier insulated bottles with hot drinks. Since it gets dark around 4PM you should plan your miles accordingly to that time to be checking in and drying your clothes to be ready for the next day.
headmask, pogies/bar mitts, gloves, wool layers with goretext pants and jacket on top. Studded tires may save your ass when going up and down the hill in Coburn Gore and Grafton Notch region in the morning when there is a slick frozen film on the road surface.