The first snowfall on Mt. Mansfield usually occurs during the first week of October. It can be a few or many inches but in general will not last. There is the possibility of deeper more lasting snow during late October. Icy trail conditions are possible on or near the highest summits during late October. Although there are good hiking days in November, expect winter to arrive.
Wind chills can drop temperatures below zero.
Expect cold rainy days, freezing rain, snow and ice. Have experience in, plan for and pack for winter hiking. That means short daylight hours, the risk of ice, deep snow, high wind, bitter temperatures. Wind, snow or ice can make travel over some sections of the trail difficult or impossible. Snow can cover the white blazes that mark the trail, making it difficult or impossible to follow the trail.