I'm a fair weather rider, meaning I'm not going to ride in the rain, much less when there's snow.
I will do some rides when the temperature starts getting cool, but I start wimping out when the temp drops to 50F for the high. When you ride in those temps the wind chill drops the temp down to 30F and even wearing good cold weather gear, it always seems like my torso is too warm and my fingers, feet and knees are too cold. I used to ride in colder temps without so many issues, so it's probably an age thing.
Having said that, enjoying (or at least building up a tolerance to seasonal temp changes ) riding in different temperatures, is just a matter of riding enough each week throughout the year that the temperature changes don't seem so dramatic.
You can buy some cycling clothes that are good for cold weather, watch those internet sales and make sure you get a good price.
The best time to buy cold weather gear is in the Spring time. 😄