Margot,
FYI, Rt 4 is the major traffic/truck route into Rutland from the east. Also lots of traffic going to Killington Mtn ski area, though if you are going in Sept that shouldn't be an issue. Rt 4 is at least in good shape, but you'll have lots of highspeed traffic going by you. Not sure of the road condition, but the little used Rt 73 out of Brandon can be used to get over the mountains, then Rt 100 to Rt 107, then over to Rt 12 into Woodstock. Woodstock is a very, very nice town.