August in Skagway is the rainiest and the windiest month of the year. In August, the weather in Skagway is typically warm. Average daily high temperature in August is about 14 degrees above zero. On average, Skagway has 22 rainy, 4 sunny, 3 partly cloudy, and 2 cloudy days in August. The rains are usually heavy. August as well as May, June, July, and September is considered the most uncomfortable time to visit Skagway.