This past Winter I did indeed continue to run barefoot. I almost didn't. I'm not a fan of the cold, and tend to bundle up. But, I found myself missing the feeling of feeling, the sensation of sensation, when running.
After running the Detroit Marathon in October, and freezing my feet off at the beginning, I took a couple weeks off. The cold came early that Fall, so by the time I was ready to start running again, I chickened out and experimented with both my VFFs and my moccasins. The moccasins worked better, actually, because I could wear socks with them, but in any case, with either, the experience wasn't the same. They were, or seemed, too 'shoe-like' and somehow I wasn't running right, or well. Either I was over-thinking the whole experience and overcompensating in some way (i.e. bending my legs too much) or because my feet were covered I was therefor 'hitting' the ground harder, but I found my feet were sore afterwards, especially my left foot (There could be other factors, like that my plantar fasciitus hasn't completely healed).
Meanwhile, over at Barefoot Ken Bob's Yahoo Barefoot Running Group, I was reading some other folks' posts on running in the cold, so I knew it was possible. I knew that I could survive twenty minutes of anything. No matter how cold, or how much snow on the ground, it seemed feasible that I could run for twenty minutes, enough to get my heart rate up a little, and get back to my apartment to warm up.
I devised a new, short, route of about that length. I could have even done small laps around the block I suppose, but I wanted to still make my route a loop, so that I would have to commit to a certain time and not chicken out. And, success: if the sidewalks were clear, the pads of my feet were actually thick enough to protect me from the cold cement, if I kept moving. Also, since I was running, I got a constant flow of blood to them and, just like in the Detroit Marathon, as I started to run, my whole body heated up. I also always did ten squats right before I walked out the door to have my blood pumping right from the start.
The tops of my feet didn't feel any more cold than my face did. Yes, sometimes that was indeed cold enough, and sometimes after twenty minutes my feet would be red and numb, but that was either on really cold days (temps below 20 degrees) and/or if there was snow/slush. If I had to run through snow, and especially slush, that tended to be very, very uncomfortable, because the non-pad parts of my feet aren't so thick.
After I got used to the initial feeling/shock of cold, and if the temp was mid-twenties or higher, and especially if the sidewalks were clear, I found I could bump up my time a little. I found a new half-hour route up around the U of M Hospital, which keeps its walkways super-clear. Also, sometimes the temps even got up over freezing, over 32, and again, if the routes were clear, I could go on one of my 45 minutes routes.
I also found that, if I couldn't run real long runs, I could at least still run twice a day: Maybe a twenty-minute run in the morning (to wake myself up!) and a slightly longer one in the afternoon when/if the temps rose a little.
So, as long as I kept the rest of my body bundled, with wicking non-cotton clothing, I was, if not fine, ok. I did lose some calluses on my feet though, because I went back to wearing moccasins/boots for walking, so this Spring I've had to build them up again. And generally, every time I ran, the cement/pavement was wet, which tends to soften calluses too. The one annoyance was rock salt. It's not quite as pokey as rocks, but it's harder to see, and some people inundate their sidewalks with it. And running on gritty salt when my feet were a little raw was not a pleasant experience.
There were also days, even maybe a week or two, when the weather was just too bad even for someone crazy like me, when it was really cold, and really snowing hard. On those days, I just stayed inside, did some yoga, and played my bass along to heavy metal albums, which does tend to raise my heart rate a little!
I ran less in the Winter, and never for any long length of time, but I did at least maintain a level of running that allowed me to still think of myself as a runner, and I didn't have to cave in and join a headache-inducing gym.