I quite like cycling in the dark. The night the clocks changed I headed out and did a 65 miler doing a loop of the Tay (from Dundee to Perth and the back on the Fife side) ... started off at 10pm :-)
Loved every minute of it. Had quite a few lights on the bike that night, and kept toggling the modes so that I could maximise runtimes. Only had to stop and change one battery and that was about 10 miles from home, which I thought was good going.
I wouldn't ride on any new roads in the dark though, and always make sure someone knows what time I'm expected back and what route I plan to take. If something happens at night, depending on time, then you can be screwed for getting help as there are usually far fewer folk about and probably less willing to stop and help. With the cold at this time of year, getting stranded or having to walk a few miles can be a serious - and potentially life threatening - problem.
I also commute all through the winter, and look forward to the cycle home in the dark ... all 20 miles of it, along country lanes for about half of it. I've had quite a few encounters with deer and bats at night.
The only thing that freaks me out a little when cycling at night is when you hit a section of road that has full tree cover, both sides and fully overhanging the road ... when you suddenly can't see the sky anymore it feels very claustrophobic.
Have been guilty of making a few animal noises at night, just for a laugh :-D
