Winter riding can be awesome. I commute pretty much year round, although last year I had difficulty keeping hands and feet warm below10 degrees F. I rode the same bike I ride as my commuter now, pretty much set up the same way. My biggest concern was ice, which I learned to spot quickly and avoid. After that it was all about layering and lighting. It's darker, people really aren't looking for a bike on the road in New England in January and layers allowed me to easily put on and take off what I needed to for temp regulation. Of course there was also the challenge of my water bottle sometimes freezing. But it's so cool to ride while the snow is coming down.