May in Portland is the rainiest and the cloudiest month of the year. In May, the weather in Portland is typically warm. Average daily high temperature in May is about 14 degrees above zero. On average, Portland has 15 rainy, 6 sunny, 5 cloudy, and 5 partly cloudy days in May. The rains are usually moderate. May as well as February, March, April, and December is considered the most uncomfortable time to visit Portland.