This is a bit incidental but Norwegian Wikipedia articles on various towns and cities in Norway will sometimes have a section in the infobox labeled "preposition" (preposisjon), because indeed in Norwegian you're sometimes "in" (i) a city and sometimes "on" (på) a city, and you just kinda have to memorize which cities are på cities and which cities are i cities: it all comes down to tradition, and has to do with the etymologies of the place names, på cities usually being named after farms, I believe.

Also, "at" the side of the road? It doesn't strike me as super weird, but I think I'd say "by" the side of the road, personally.

Also also, in my conlang I obviously made things much simpler by just using one preposition for more or less every locative sense.