I think the dirtiest my soles have ever gotten was from walking around an outdoor mall in Phoenix, Arizona. I suspect the lack of rainfall, after all it is the desert, contributed to the buildup of dirt on n the sidewalks and walkways
Hiking through mud after it rains. I make sure to make multiple passes through the best muddy patches so my feet get completely covered in mud.
My feet get the dirtiest while on nude hikes in the forest and walking through the mud and dusty paths.
I think i already did mention this in another thread. I think the most dirty feet I ever got was during a school trip to Paris, mainly by using the metro (subway train). But i guess they improved their station maintanance since then, as at two later stays i didn't get more filthy paws than in any other major city. I was told the dirt then came from the brake abrasion of the trains that spreads on the platforms.
The soles of my feet are regularly black when I take the train to the next big city. The platform in our train station is so neglected that my feet are covered with dirt already there.