October in Jamestown is the rainiest month of the year. In October, the weather in Jamestown is typically warm. Average daily high temperature in October is about 13 degrees above zero. On average, Jamestown has 20 rainy, 7 sunny, 2 cloudy, and 2 partly cloudy days in October. The rains are usually heavy. October as well as March, April, May, and November is considered the most uncomfortable time to visit Jamestown.