I have done some early am rides in the past for some of the same reasons. I would usually get up at 400am-ish when I was riding 100+ mile training rides. It's peaceful.

I'm attending a charity event in Boston tonight and will be riding 32 miles home afterwards. I plan on leaving the event by 2am at the latest, than once I get clear of the city it's straight sailing down a rural route the last 20-25 miles home.

My only concern is that my route takes me past the access road for a max. security prison and tends to be a lot of cops in the general area, looking for anything out of the ordinary. I hope they don't hassle me for riding in that area at night.