I've never done any sort of road bike night riding. I've done lots of mountain biking at night (including some racing). It just sounds so much scarier on a road ride. Mostly because of the speeds involved and because of any cars. Night mountain biking is really fun. Even trails that you are really familiar with seem so different in the dark! In the winter I sometimes ride with a weekly group night ride. We've had as many as 20 or 25 people riding. It's cool to see a long line of lights snaking up a trail! Good lights are pretty expensive, but they are worth it for those of us (me) who have very poor night vision.