Big question: does anyone follow a particular strategy for keeping their feet dry in winter? I'm always concerned about running in slush or soft snow and getting it on the mesh portions of my shoes, since they aren't remotely waterproof. I realize I might be overthinking this, considering I did the last two miles of my recent 6 mile walk in the rain and my feet were fine. But that was summer, not winter. My options for running shoes that fit me correctly are very, very limited because I wear men's sizes but most men's shoes are too wide for my feet, so buying different shoes for winter is a difficult proposition.
My other big concern that held me back last winter was darkness + ice. We often have winters where the snow doesn't fully melt before it drops back below freezing and/or dumps more snow on us, so we'll have weeks, even a month or more at a time where there's a hard-packed layer of frost on the roads and sidewalks. Sidewalks don't get plowed, period, and the residential streets I'd be even remotely comfortable running on typically don't get plowed, either. Then, too, it's dark when I go to work and dark when I get home.
What I did learn is that the trail at the park gets plowed pretty regularly. The parts of the riverside trail outside the park are a lot more iffy, but that gives me a 1.33 mile loop if I'm willing to drive ten minutes (in warmer weather I make the trip there part of my run, but, well, see above). That works okay for daytime long runs on weekends, even if it's boring doing the same loop too many times. Still better than going to the gym and running on a treadmill (I kind of hate going to the gym, like...a lot). Haven't tried it at night on weekdays; my solution last winter was to put a rowing machine in the basement and substitute it for my midweek runs. It's a lot easier to convince myself to row in relative warmth with my good sound system next to me than to convince myself to go out into the freezing night, you know? And since I only substitute it for the shorter workouts I don't run into the treadmill boredom problem so hard. Would have bought a treadmill instead, but the ceiling is too low in the basement and I don't have anywhere else to put exercise equipment, so cross-training it is.