Riding a motorcycle when it's that cold can be done. First off, buy heated gear and heated grips. We use Gerbing brand jacket liners (about 200 bucks) and socks (about 80). I also install Gerbing Thermostats on our bikes (about 100 bucks). The Gerbing products work so well you have to be able to control the heat. I've installed Oxford brand grips (80 bucks) on a few bikes and they work great. Also look at Oxford muffs. You have to get your wallet out but it's worth ever cent! I rode my Goldwing 250 miles on a 27 degree day. It's like riding in a hot tub. I ride with the jacket liner close to my body and insulate it with a jacket on top that blocks the wind and holds the heat in. Once you ride with this stuff you'll never ride without it again. I'm no Harley expect but I would think a Harley would make enough electricity to power it all. Research it. If you need more power you can change the headlight and other bulbs to LED. I had to do that on my KLR650. My real concern is the crosswinds. I wouldn't ride in that. You could get blown into a car. Also I would worry about the wind blowing parts off a Harley ;) PS: Sorry about that joke ;)