It's showing him Wawas he's been to before. That's what the clocks mean. For the search "wawa" it doesn't make a lot of sense to prioritize history over distance, because Wawas are nearly identical. But for "farmer's markets" this would probably be a useful feature. Figuring out how to differentiate between those two examples algorithmically is super non-trivial though
This is incorrect: the clocks mean he has selected those search results before, not that he has physically been there. Source: Just tested this in-app.
Maybe he looked at a location first for information, and to know where it is, and needs to look for it again at a later time to actually go there.