Timothy didn’t find any cities, and in a way this was a good thing, however, even though he didn't find any cities, towns, or villages, he still found a group of humanoids! The humanoids lived in dens, and thus, it meant that most technology eluded them.
“I can't believe I found a bunch of cavemen,” He thought to himself, as he followed the group, up from the sky. “Ortana did say that she saw cavemen before, I just didn't think that they'd be in our damn backyard. This is insane!”
Timothy curiously followed them, and scared them shitless at the same time, because these cavemen were terrified of Billy, the dragon. A flying dragon seemed like a terrifying monster to them, and that wasn't surprising, on the count that they were isolated by their surroundings here. He, and Billy scared them beyond measure, but he felt the need to observe them for a while, so he kept following them!