Being a floridian I dont own winter gear, so the warmer the better for me. Ever since I took that stupid blower off Ive wondered how long it would take me to get a good out of state ride in. It is a bit far off, but I'll be a contender depending on money and work status.
I go every year in the Spring & Fall. The middle of April usually provides the best weather. Temps have started to warm up a bit by then, and in a "typical" year, May is a rainy month.
Just for reference, here is the historical data for temps and rainfall by month for Maggie Valley. As we all know this is still hit or miss. Oct. is supposed to be the dry month and we got rained on ALL last weekend. Still a fun trip though.