If you’re looking forward to lots of outings with your partner, check out these details about year-round temperatures in Skagway: The hottest months are usually July and August with an average temp of 50°F, while the coldest months are February and December with an average of 19°F. The snowiest months in Skagway are December, January, February, and November, with each month seeing an average of 31 inches of snowfall.