Used to do quite a bit of night time road riding, solo and with others. Less so now although there are plans to do a few group road rides over winter.
Years ago I had a 25 mile commute through the North Lancashire/South Lakes lanes which was lovely at night. Much safer on the roads too. Far fewer cars and what there was could be seen coming a mile off. I think the worst points of night-time road riding is going through rural towns or villages at 11pm or so when all the drunks are coming out of pubs and people are driving home (sometimes not entirely sober) from meals out.
Funnily enough, most of the drunken shouts you get now are more positive than anything – last ride I did with a mate we got all sorts of variations on a theme of “GO ON BRADLEY!”
Last solo ride I did was back in about April; left the house at 11.30pm, got back at 2am. The only people out were workers on the railway, they looked at me in a proper “WTF?!” manner. 🙂