Actually, regarding 101, once you get past Milford/ Amherst into Wilton it's a very good road to bike on. The hill going up to Pack Manadnock/ Temple is good fun. 101 will run into Peterborough and eventually into Keene (the intersection of 101/ 12 and 9 can be dangerous). If you survive, Rt 9W will take you into Brattleboro and you can figure your own route from there.

I like using Google to map out a lot of my routes.

Good luck, that's a long haul from Salem.