The "wagers" in the title of this post refer to the weather-based decisions a bicyclist must make before venturing out in temperatures near or below freezing. A slight difference in road surface temperature or moisture can mean the difference between safe and unsafe riding. The weather report from the airport or downtown might not give an accurate picture of the conditions you will encounter on your ride, even just a few miles away. For example: It rains in the afternoon, with temperatures above freezing. Overnight, the forecast calls for temperatures dipping to the upper 20s to low 30s. If the temperature stays above freezing through the night, or if the roads dry before the temperature drops below freezing, you can have an ice-free ride to work the next morning. If the roads stay wet while freezing temperatures set in, you can encounter icy roads. You need to guess, based on the morning weather report and the conditions on your own street, whether it is safe to ride in the morning.
Also, you need to learn your own tolerance for cold temperatures. For temperatures from the low 40s down to the upper 20s F, I can ride comfortably wearing nothing over my face other than a headband under my helmet. Below about 28 F, I replace the headband with a fleece helmet liner, and I need to wear wrap-around eye shields rather than ordinary eyeglasses to keep the bridge of my nose from painful cold and to keep my eyes from watering. To ride in the low 20s and below, I need to cover my nose and cheeks with a folded bandana. If I fail to use these precautions, I will have a very uncomfortable ride.
I guessed wrong on December 23 on the trip home from work. At 5 PM, the National Weather Service posted a temperature of 34 F with rain, so I thought I would merely have a wet, but not icy, ride home. I didn't account for the fact that the temperature had been well below freezing for 2 days. On the way home I hit a slick spot that nearly caused me to crash. I coasted the last few blocks at 5 mph, with my feet off the pedals. Regardless how much bicycling skill you have or what type of bicycle you ride, I urge you not to try riding in potentially icy conditions. One unlucky combination of ice and traffic could ruin your life.
Not to end on a dire note - I enjoy riding in the winter. The cold air makes me feel more alive, the roads often have less traffic, and everything looks clearer and brighter in the absence of the summer haze. Riding year-round means that I never need to talk myself into getting back on the bike in the spring, and starting a spring ride at a temperature of 45 F feels like a walk in the park!