Randonneurs do this regularly. For long nighttime rides, dynamo hubs and lights are common. Riding your bike becomes a jump-on-and-go affair. No more worries about whether your lights are charged. The added bonus of dynamo lights is that the headlights are almost all shaped beam lights. In contrast to round beam lights, a shaped beam has a cutoff. So the light you generate goes where you need it instead of sprayed everywhere. Also the top of the cutoff is the brightest part of the beam pattern. So you're putting more light farther down the road and less on the ground closest to your bike. This helps with visibility and preserving night vision.

Okay, so maybe a dynamo setup is out of your price range. For the price of a proper dynamo, headlight, and taillight, you could own two each of the Trek Commuter Pro RT and Flare RT. They even come in a package deal. Run one set while you charge the others using a GaN battery pack (GaN batteries can charge the lights before the ones in use are dead). And the Computer Pro RT has a great beam shape, as well as a true high beam-low beam mode (different beam shapes). I tried this setup on one of my bikes because I didn't have time to build and tweak a full dyno setup ahead of a big tour. Cool added bonus: both of the lights communicate with each other. Turn on the headlight and the taillight automatically turns on. The remaining charge indicator on the headlight also shows remaining charge on the taillight.

Finish out your lighting kit by mounting a good LED light on your helmet. I'm partial to ThruNite TC15 V3 in this context. It will run for almost a month in limp mode, which is enough light to read a map, cue sheet, and street signs. The next level up is equivalent to most cars' low beams. Yes, it's a round beam, but the beam pattern is excellent for bicycling. Carry a spare 18650 cell in a case (no fires please).

Dress for any temperature differential, i.e. technical fabric layers suited to the high and low temps. I'm partial to merino wool because all the reasons. Use a reflective sash, ankle straps, and if you're in the US, a reflective strap on your left wrist for hand signals. Vests are very visible, but not something you want to wear for long rides.

Know your hydration and caloric replacement needs. If you're riding somewhere remote (which makes for the best overnight rides, IMO), resupply may not be possible. Tune your loadout accordingly.

Know how to repair your bike on the side of the road. Cold. Test out all of your toolkit. If you don't enjoy wrenching on your bike in the comfort of your living room, with a tasty beverage nearby, imagine your morale on the roadside, in the rain, in the dead of night. And now you see another good reason for the helmet light above.

Source: am randonneur for 17 years now.