May in Ashland is the rainiest month of the year. In May, the weather in Ashland is typically warm. Average daily high temperature in May is about 14 degrees above zero. On average, Ashland has 12 rainy, 8 sunny, 8 partly cloudy, and 3 cloudy days in May. The rains are usually heavy. May as well as January, March, April, and October is considered the most uncomfortable time to visit Ashland.