I ride, a bicycle, in Wisconsin, year round…
In my discussions with cycling friends who only ride in fair weather, here is my conclusion. I will assume they are like other normal people and are a good sampling of the population.
They don’t ride in the winter because: It’s cold, and slippery, and cold. I did have a concern or two about their steeds and the salt, but mostly, it’s cold.
My answer is usually a question. You live in the midwest, it gets cold here, you don’t seem to suffer from bouts of hypothermia, how do you stay warm? And thus, I answer their biggest problem with riding in the winter.
Second big problem is usually the snow and ice on the roads. This is the more complicated answer, one most cyclists enjoy though. Buy stuff for your bike. This is a list of possibles:
Studded tires- they just work. Carbide studs last a long time. Tires are easy to change, most cyclists should know how to fix a flat.
Fenders- there are easy to put on fenders using rubber straps, some snap on to the frame or, have permanant ones put on. I reccomend having a shop put them on. They can be a pain to line up.
A bag- any bag you can carry an extra layer of clothing, batteries for lights (I assume you have them already) and other bits of bike nessessity. I use a Messenger bag but any backpack, bike trunk or pannier bag works. If you need water proof, use ziplock bags.
The big thing that I have added to my bike for cold weather riding are:  POGIES! – these are the big handlebar mitts. Every type I have tried are warm, some are not waterproof.  Everyone I know who has them becomes a winter rider. They range from $20 for ATV mitts to $100 for the super Alaskian type. I generalize extremely, just search for ‘bicycle bar mitts’ or ‘pogies’.
You don’t have to ride in the snow. The streets clear off a couple days after a snow and are quite passable. Riding in the snow can be challenging, expecially when there is loose snow to go through. Mostly, keep yourself kind of fluid and roll with it. Momentium will get you through, always ‘be ready’ for the bike to slip when going through the loose stuff or over ice if you don’t have studs.
Simple answer to riding in the winter, in Wisconsin. Wear warm, layers work best but, any warm will do.

Look for the next article: How I ride in the winter- The gear.

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