January in Woodstock is the windiest and the coldest month of the year. In January, the weather in Woodstock is typically cold. Average daily high temperature in January is about 6 degrees above zero. On average, Woodstock has 13 rainy, 9 cloudy, 6 sunny, and 3 partly cloudy days in January. The rains are usually moderate. January as well as February, March, April, and May is considered the most uncomfortable time to visit Woodstock.