January in Woodstock is the cloudiest 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 11 rainy, 10 cloudy, 8 partly cloudy, and 2 sunny 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.