I had a century ride I did for a few years in mid-October in Western MA. Getting started at around 7:00 or 7:30 it was invariably in the upper 30's to low 40's. On a really good day, it did break into the low 70's by the end of the ride. For my legs, I wore leg warmers and just kept them on the whole ride. On top, I had a long sleeve base layer, a cycling jersey, and a light wind-breaker/shell jacket. I would be chilly probably the first hour, then comfortable, then got warm. When I got uncomfortably warm, I stuffed the outer jacket in my jersey pocket. Was still a bit warm in the latter part of the ride with the temps higher but, on balance, that compromise worked ... chilly at first, warm towards the end, and pretty comfortable in the middle.