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Winston-Salem benefits from a great temperate climate. Summers are hot, spring and fall are comfortable, and winter is very mild; the city rarely receives snow.
Summer months usually range in the mid 80s. The spring and fall see very nice temperatures ranging in the 70s while the winter gets down occasionally below zero but can stay in the 40s. The city feels protection from the mountain range nearby from the truly cold weather. The city sees the most rain in the summer and although it is humid, it is not terrible when comparing to states and cities further south.
From worldclimate.com, here is some data:
The summer is filled with activities and is the tourist season. Music concerts take place from May through Labor Day downtown; visit http://www.visitwinstonsalem.com/ for more information. There is also a great fourth of July celebration and National Black theater; for more information, read the events & festivals page.
Yet at its opposite, the winter is also a beautiful time to come to this city. The Christmas decorations are gorgeous and the old world feeling that Old Salem sets up is definitely worth a visit. Also of course, the spring brings in beautfiul flowers and the fall, colorful foliage so any time of year is really a great time to vist.