Nice, a bowling pin milk! Those are usually pretty early, I'm guessing this one is from the 20s when the dairy first opened. They seem to have been phased out by the 30s. I've got a few from dairies in Quebec and all date to the 10s or 20s as far as I know.
another picture so you can see the distinctive shape , the other 2 were from the auction site
agree it would seem to be from the earlier years of his operation , likely 20's or 30's , most of the local milk jugs I've seen for this area are from the 40's - 60's , I've rarely come across anything earlier , a few of the local towns I've never seen anything 20's-30's era , I think this would be the earliest jug I've seen from Bracebridge