Winter is not a favorite time for cyclists. It doesn't mean you have to hibernate in your cocoon until the Spring thaw. You do have to plan more. Checking the weather first helps you decide what and how much layering you will need. Don't completely count on the weather forecast as you know how that goes. Overdressing is my motto. Don't expect to break any time trials. The air is thick and will slow you down. In fact I suggest you leave your fast road bike in the garage. You will be more comfortable on a hybrid type bike. All those extra layers of clothes will weigh you down. Thick warm gloves will make shifting more difficult. A roomy pair of shoes or boots with wool socks on Bmx pedals will keep your feet warmer. I don't believe you need to purchase expensive Winter cycling clothes. Fleece sweatpants, gloves and hat over your ears work well for me. You will look like the abominable snowman. Also don't expect to do any high mileage. My rides seem to average around half. For me windy grey days are the worst. Temps below freezing are also a struggle. I would rather ride 6 miles to the store than not at all. Today's ride was 25 miles and temps never got above freezing. It was difficult but doable. When temps reach 40 it will seem like Spring.
Old Man Winter will not get the better of me.