Street photography in small towns

I think that street photography as a practice by certain well-known photographers, while not impossible outside of large cities, is very challenging, which is why I believe that the street photography workshops I find online are often hosted in larger cities. Specifically, I think street photography is challenging in wealthy, mostly white, small towns like Princeton, Hopewell, etc., in New Jersey. And impossible in places that have no walkable downtown, e.g. Montgomery, West Windsor, etc.

I have tried many times. When I point the camera in the direction of a person, they immediately stop to either remove themselves from the scene or give me a look that feels to me like, “what the f**k are you doing”. NO ONE CARES when I do the same thing in New York City or Philadelphia.

I am not comfortable with street photography in general. Still, if I were to spend an hour or more walking around taking photos of people, I would soon have a police patrol car following me around and beyond that being questioned as to the reasons for my actions.

Is this image of skateboarders on Scudders Plaza street photography? There was no street here. I interacted with them. We chatted about camera equipment and the best angle and shutter speed for these shots. These skateboarders didn’t mind my camera.

Would the father in this image get upset if he noticed that my camera was pointed in their direction?