Lost and Found overflow – Step aside, ma’am, we’re racing

Bill Schulz recently sent along this photo which he inherited, but which came with absolutely no information that would help him identify the car in it. Bill writes:
If the photo’s from my mother’s side, it’s probably in the Kerhonkson, NY, area. If my father’s, probably somewhere around Poughkeepsie/Pleasant Valley, NY.
That is probably my paternal grandmother […]