My great-grandfather, George Thornton Metcalfe, did the striping on wagon wheels for a living in the late 1800's/early 1900's (he died in 1918.) He lived in Bergen and Hudson Counties in New Jersey, so while he probably worked in New Jersey, it is possible that he worked for a New York company.
I know very little about the occupation so far; although I did find a book, The Complete Carriage and Wagon Painter by Fritz Schriber, published in 1895. Unfortunately, I just found it recently and haven't had a chance to read it yet. Does anyone know anything about this particular occupation, or have any ideas about additional research sources?