I second the pre-dawn riding. It is peaceful, there's less traffic and there is something very cool about riding as the sun comes up.
I swore I would never ride in the dark, but I started bout 3 years ago. I bought a light that was better for the "to be seen" category, and that didn't fly in the semi-rural suburb I live in, with very few streetlights. Got a better light and went from a 4 mile ride home from the train station on my hybrid when I was going to grad school, to 10-20 mile rides starting anywhere between 5 and 6 AM on my road bike.
It does require cold weather gear at this time of year, but I already had that.
I would suggest getting used to riding on the road. It's actually easier to do this early in the morning. Trails are OK, but as you progress, you will start getting annoyed with the walkers, strollers, roller bladders, dogs, etc.
2015 Trek Silque SSL
Specialized Oura
2011 Guru Praemio
Specialized Oura
2017 Specialized Ariel Sport