Mostly because the road system was laid out by a drunken cob-web spider with romance on it’s little mind. Nor is there any discernible rhyme or reason to the numbering system, when they bother to number them. Changing the names of the roads at random intersections doesn’t help much either.
That sounds like my neighborhood. You can’t use your GPS to find things here because the directions the locals give you involve landmarks that no longer exist. (Well, you go past where the fruit stand used to be....) Additionally, distances are measured in minutes, not miles. (You have to put yourself in the mindset of a retired moonshine hauler or NASCAR driver.) The drivers here are pretty good, but they travel fast on these little winding roads.