Have had plans the past 2 yrs to superbowl it up in Feb if the weather stays 45 or higher. Last year, here in DC, was a promise until the end of Jan when it started to get into the 20s for daytime highs. Bad timing considering the 2 months prior were 40s and 50s (unusually warm).
Other than that, I can't see dragging the gear out for a regular movie. Although, I'm sure the Express train was way cool when it first pulled up. That has a tendency to knock pics off my wall indoors.
I managed to get 2 Monday Night Football showings in during October and was happy with that. One night was in the 50s, the other was upper 70s. HD outside was amazingly clear for 196" screen.
I use the winter to try and improve my setup. This mainly refers to setup time in terms of better, quicker screen frame setup, etc. I meant to run speaker wires in the ground last winter and never got around to it. Might have to do that this year.