When a backroad route I'm not familiar with presents itself, I strive to assess the totality of the circumstances. That includes weather, road conditions that I can see or find out about, the vehicle I'm in and it's condition, how likely I am to be able to communicate if assistance is needed, the likely time it would take for assistance to reach us, and fuel state. Road conditions in particular need to be reassessed continuously, never going further than you can safely turn around and never being embarrassed to say, "Nope, this looked good before and now it doesn't. We're going around the long way."

In daylight with good weather, the right vehicle and other conditions I'm willing to be cautiously adventurous. Darkness, bad weather, the wrong vehicle and so on will cause me to make different choices.