For chicks hatched in the spring, they molt quite a few times as they grow, but they usually skip the big fall molt.
For adult chickens, that have already been through one winter, they do tend to molt sometime in the fall, so they have nice new feathers before really cold weather arrives. Sometimes they do a gradual molt, just a few feathers at a time, so they are always fine. Other times they lose almost all their feathers at once, so they look really awful and miserable, but they grow all the feathers back pretty quickly, so they are typically done in a much shorter time than the ones that molt gradually.
Ideally, that "fall" molt would happen before cold weather. In practice, sometimes a hen will do it in the heat of summer, or wait until the cold of December or January. So they sometimes get the timing a bit off, but usually seem to do OK anyway.
Windward side is where the wind is coming from.
Leeward side is the opposite side, so it is the most sheltered one.