The best time to be cleaning gutters in winter would be right at the beginning. This is at the time of the year when leaves are beginning to fall, and the rain is not as harsh as it’s going to be. Creating conditions to keep your gutters clean is easier than constantly having to clean them. Trimming your trees is a great way to do this as it prevents loose leaves and debris from clogging up your gutters. If there is an issue, it’s better to get it sorted out early than to let the issue become worse. At the beginning of winter, the contents of your gutters shouldn’t be frozen, so most things should be easy enough to take out.