October in Windsor is the rainiest month of the year. In October, the weather in Windsor is typically warm. Average daily high temperature in October is about 14 degrees above zero. On average, Windsor has 13 rainy, 7 partly cloudy, 6 cloudy, and 5 sunny days in October. The rains are usually moderate. October as well as January, February, March, and April is considered the most uncomfortable time to visit Windsor.