Lots have a ready answer to that question: certainly not! Cycling is fun when it’s 80 ͦ outside, but once it’s below 50, not so much. In the 30’s, you gotta be crazy. So if you belong to that crowd, spare yourself the next 5 minutes of reading, because you know you don’t want to ride in the cold.
I have done a lot of extreme things in my life, including cross country skiing, ski mountaineering, snow camping, and running and hiking in all kinds of weather. So I’ve tried to keep an open mind about cycling once the weather gets cold, and I think it can be a lot of fun. Lots of things change when the leaves fall off the trees and the corn and soy beans are harvested: we don’t get so much protection from the wind. It’s not green (and not those bright autumn colors either). It’s austere; you can see views that are obscured when the trees are in full growth; the color spectrum is more monochrome. You notice the sky, the clouds, the low angle of the sun. You notice that when you’re riding into a stiff wind, it’s pretty cold. But the countryside is still amazing and lovely, just in a different palette and with different kinds of vistas. You have to time your rides to make the most of the light and warmth, and avoid being on roads where you’ll be backlit by rising or setting sun, because drivers have a hard time seeing you (and they’re not expecting us to be out riding in November or December, so they’re not looking for us).
Let’s assume you want to give it a try. The important thing is to dress appropriately, and to be prepared to deal with mechanicals efficiently, because you’ll get cold in a hurry once you stop peddling.
Here’s my advice about how to enjoy this experiment: dress in layers. (Note: you aren’t aiming to look chic, and you won’t, because you’ll have 4 or 5 layers on to stay warm. Also bear in mind that it takes more time to get ready to walk out the door when you’re wearing this much stuff, so build it in to your calculations! Consider dressing in high-visibility colors and using a rear light that’s readily visible, because winter light can sometimes be dull and overcast.)
Should you try this? Depends on how much you want to get out and ride, but I’d say, give it a try, especially if you can find a companion or two to ride with, and perhaps schedule a stop somewhere in the middle of the ride to warm up and eat a snack and drink some coffee or hot chocolate (the Klein Brot Haus, for example, or one of those grungy convenience stores with tables set up inside where cyclists and old guys accost one another). I’ve been immensely satisfied by beautiful rides that started out a mite cold but were reasonably comfortable after I’d been in the saddle for 15 minutes. I think you’ve got to dress for these adventures; if you don’t wear the right clothes and you’re cold the whole time, you’re not going to like it!
No doubt others would give different advice, and indeed, everybody has their own personal response to cold and heat. Some people don’t like being out in cold weather, hate the feeling of shivering and tensing up because their bodies are chilled, get their feet or hands cold and can’t ever seem to warm up. Others hardly notice any discomfort. Pay attention to where you fall on this spectrum. If your body thermometer runs cold, add another base layer and wear warmer socks and gloves. Invest in a warm fleece or outer layer. If you have friends who always wear the same basic outfit on days in the 40s, and they appear to be comfortable, ask them what they’re wearing. Once you get your clothing dialed in, you may find yourself riding fairly often, and really enjoying the change of seasons. If you don’t, there’s always Zwift or spin class!