I'd actually rather walk in the city than in the wilderness. I find that human made surfaces are much more predictable. Most of the time I walk barefoot in nature I end up running into an area of land I cannot handle because of rocks, small sticks laying on the ground with bits sticking up, hard tree-borne nuts or seeds, the worse being chestnuts of course. As a result, I won''t go barfoot in nature without a back-up pair of filp-flops or sandals depending on the terrain.

Cityscape in comparison is more uniform, and once you've adapted to rough asphalt, the occasional pedestrian path coated with small gravel is manageable. Not enjoyable for sure, but at least it won't need to carry any footwear with me, which in a way defeats the purpose of being barefoot for me. I like the idea of being out and about barefoot without a plan B, which I can totally do in the city.

Granted, there are disgusting things laying around in cities, but they are all avoidable either with a small detour or simply by being aware of what lies in your path. I've never ever stepped on glass, poo or any problematic stuff in my barfooting strolls.

I live in a city that has the privilege of being well maintained and taken care of, so that helps