It's a Hiram Walker & Sons whiskey bottle from Canada. I'm not sure how long they were made like this, but I'm guessing it's from the 1930's-40's. I dug one like it in a 1940's dump.
Because it's a Canadian bottle, it's not required to have the Federal warning on it. Some bottles may have the warning if they were made for export to the US.
this bottle is made from the mid 1920s to around 1932 or so .the design got a little smaller and the crown diapered . your bottle is Canadian and was bootlegged over the border during probation.
Yep, we find those all the time up here. I'm sure a large number of them were smuggled over the border as well. The fact that it says it's a US pint suggests to me that they had an idea of where it was going to end up as they were producing it. From what I've read the Canadian distilleries made little effort to hide the fact that they were producing liquor to be smuggled into the States. Even during prohibition in Ontario the distilleries were allowed to remain open for the "export market".