The only story we have set in the 20th or 21th century are “~~Return to Tomorrow~~ Tomorrow is Yesterday”, “Future’s End”, “Future’s End, Part II”, “Carpenter Street”, “Tomorrow and Tomorrow and Tomorrow”, PIC season 2, and First Contact. If there are more, they escape me. These stories are all set on Earth. My best assumption would be that after the 21st century is when automobiles got phased out of society. There isn’t really a good reason to show roads when cars aren’t a necessity for travel.
However for whatever reason, as Mariner points out, we still have bridges.
Considering the tiny holopods used in “ I, Excretus” could be monitored, why didn’t people try to view holodeck monitors during other situations where they know something has gone wrong? Wouldn’t that be helpful?