Winter Biking in Wisconsin (and other northern spots)

I might not be the fastest tri-head on the pavement, but I can tell you how to have a good time over the winter. If you don't grab your bike on any or every given Saturday throughout the winter and regardless of weather, you're missing out. You can ride your trainer or rollers every other day of the week if you wish. Once in a while you need to unhook and get some fresh (even if freezing) air. Here's how I do it.
First, no excuses. "But it's too cold". I don't want to hear it. All sorts of folks ski, snowboard, run, climb mountains, and the like in weather way worse than you're already not going out in. We'll make a clothing list below. I consider it imperative that you keep at least 4 things warm. Head(ears), hands, feet, and what's under your shorts.
Second, winter riding is about being prepared. If you're not organized, it will take you three times as long to suit up as it will to actually ride. Prepare, and you'll be more likely to repeat the process next weekend.
Third, it's nice to keep your legs in shape with your bike stapled to the trainer, but there's no substitute for outdoors.

Let's make a shopping list. For your head:

• Balaclava - If you're riding in the cold, I consider this a lightweight must have. It fits under your helmet just fine. Keeps those ears warm.
• Shades. Something to protect your eyes when it's sleeting. Note, you probably want clear lenses too, because it's often dark in the winter months.
• If you're hardcore and go out when there are negative numbers on the temp scales, try ski goggles.
• I recommend a helmet in all months. Frozen pavement is hard.
  

For your feet:

• Smart wool or your favorite warmest socks (maybe even 2 pair).
• Is it wet/snowy/rainy ? Dry equals warm. Get some of those high zoot $50 boots to cover your shoes. Short on the extra fifty? Sandwich bags over your socks will do in a pinch.
• Mountain bike shoes. If it's slippery or icky out, you don't want to be walking around in shoes that feel like ice skates in dry weather. Exception to this rule, I went out yesterday in 40 and rain/sleet. It wasn't slippery out, and my mountain bike shoes happen to hold significantly more water than the road shoes.

For your hands: I have three different glove configurations, depending on how cold it is.

• Regular fingerless cycling gloves.
• Add those one-size fits all, 99 cent, Walgreen's gloves under the cycling gloves.
• If it's really, really cold I have some winter cycling gloves that don't look much different than those big puffy winter gloves that you wore as a kid. Only difference, the ones I had as a kid were neon green.
• I have also been told good cross country ski gloves work great, but I found the cycling gloves cheaper than the ski gloves. I'm hear that's abnormal. Your mileage may vary.
  

For your nether regions:

• Caveats, I'm not sure I have this one totally nailed down (based on experience). I have no clue if it's much different for women, I'm guessing not.
• Layers is good. I often hear (in summer) you don't want to wear underwear or 2 pair of shorts, etc.. In winter, you want at least one cycling short layer and some good tights. I say "good tights", because I have a good pair and a cruddy pair. It's worth the extra 20-30 dollars to get some that don't ride down and have a draw string in them. The "goodness" factor may be more about material than anything. Let's just say the "not-good" ones can ride down your legs and get caught on your seat during an otherwise decent cyclo-cross dismount.
• These two layers may not suffice. Think extra underwear (thermal). And/or windscreen type shorts that could go between the tights and the bike shorts.

The rest:

• Once you have the four key parts covered, you just need a decent base layer and something to cover. Here are a few notes.
• You can buy cycling specific winter gear. It's great, but you will pay for it.
• As it gets colder, here's the order I add to my upper body. Bike jersey, athletic thermal underwear (long sleeve), jacket or vest. And on really cold or wet days, I'll toss a sweatshirt under the jacket.
• I used to wear just bike shorts in anything pretty much over 50F (for sure over 60F). I have heard from folks smarter than I, that you need to keep your knees warm in weather like that to avoid injury. Those folks said, "something on your knee" for anything under 70F. Something would be either bike tights, or knee warmers.
  
• As usual, watch for anything baggy that might catch on your bike (or a race spectator with a big fingered #1 glove).
• Don't forget to stay hydrated, this might mean putting a camel back on your list so your water doesn't freeze.
• Check the weather before you leave... If you leave covered for 20F and the temps drop significantly, it's more than annoying. It's dangerous.
• Put any pager/cell/lifeline you might have in a sandwich bag. Dry cell is a happy cell.

End notes. Winter riding is one of those things some people never do and don't know what they are missing. I'm not saying you should go out riding 20mph on an inch of ice for your first winter ride. Just consider, folks have done much crazier things than ride in 20 degree weather. Some of my most memorable rides, are in a pile of snow. I may have only covered 4-6 miles on my mountain bike in a hour, but it counted tenfold toward my general bike-ed-ness. Just get out there, even if it's only long enough to shake that "stuck on the trainer" feeling.

Good luck. See you in the spring. For more reference, from way crazier folks than I, see Icebike.org