Horses are graizing in the field – field seen as an enclosed area of land
Tiger Skirt-Chaser was practising on the field – field seen as surface for sport
The same goes for streets.
He left his car in the street for two hours.
They were reparing the holes on the street.
I’m sitting on the grass – surface, the grass is short
I’m sitting in the grass – volume ,‘more enclosed area’ - the grass is long
The contrast is still about ‘on’- surface and ‘in’- area but usage may vary from speaker to speaker and context to context.