I've been night riding for decades, so I can offer this advice: do not skimp on the headlight! There's no such thing as too much light since advanced warming of road imperfections and debris is very necessary. Get a good light. They're expensive, for sure, but worth every penny. Second, put on some "tough" tires. The last thing you want to do is change tires in the cold and dark. I switch to Conti GP 4 Season tires every fall and run them until spring. They're excellent. I've never flatted one, and they really do ride nicely. Not as fast or supple as the 4000s II, but not bad at all. After that, well, dress warm and enjoy the ride! There's no need to stay indoors just because it's dark or cold.