For randonneuring rides, it's pretty normal to jump from 200k to a 300k with no intermediate steps. If you're not supposed to be on it at night, I'd just go find a good route that you CAN ride at night rather than sticking to that one. If they catch you and fine you, do they make you leave the trail, or how does that work?
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"be careful this rando stuff is addictive and dan's the 'pusher'."