I did a tour in Vt. in mid October. It was a long weekend tour and most of the other people were from the midwest and tri athletes; cycling was not their firts sport, it was clear they were runners. They came in cotton socks and shorts! We came with tights, LS jerseys (wool), rain jackets, booties, wool socks. It was 38 in the morning and never got above 50. I know it was a few weeks later than you are planning, but i would go on the side of being cautious. I am always cold, too, even on the climbs.