Given the age of the kid, these are the only two possible dates.
My first choice: April 1952
The splotch where the month probably is is about 30% larger than the splotch where the year probably is.
Not knowing anything about the font or kerning, I just did some experimentation, and found a number of fonts in which the space taken up by all-caps “APRIL” is about 30% larger than the space taken up by “1952.” I couldn’t find any that made NOVEMBER or SEPTEMBER only 30% larger. (From the relatively uniform month splotch, I’m assuming all-caps.)
Second choice: September 1953. Less likely but two points that make me not wan to summarily dismiss it:
In some format of calendars, the Sundays and holidays are printed in red. You can notice that the column for Sundays is very dark.
Similarly, the column for the first Monday in the month is dark, possibly indicating Labor Day.
That said, I agree that the size of the first splotch doesn’t reconcile well with the size of the year splotch for September, but compression artifacts can be weird like that and, who knows, maybe the calendar maker didn’t use exactly the same font for the month and year.
If you look on the calendar in Colophon’s link, it looks like the letters in the month name are closer together than the numbers in the year. But that one is in lower case though.
A Google Image search for “1950s calendar” comes up with several similar designs. It looks like there was some firm that produced calendars like that for companies to use as promotional items. (Edit - the one linked to is actually from the 1960s, but the point stands.)
Any idea where it was taken at? If we could narrow down a city and state, we may be able to find a calendar from a business in that city online somewhere.
I’d agree with the “September” identification. It looks like the calendar has the weekend dates “dimmed out” and the first Monday appears to be similar, which would make sense if it’s a legal holiday.
My first thought was those were flying birds in the foreground (a pheasant hunt perhaps?), but on second and third thought they could be anything. I even had a thought it might be a harvest painting along the lines of Millet’s The Gleaners or the The Potato Harvest.
The only month that works for me, provided it’s in the same series as the pictures provided above, is September 1953.
Zooming all the way in, the dates seem to run from having the first be on a tuesday and the last day being on a wednesday. In the time frame, that’s only September +/- 3 years.
The second tuesday is much darker - hardly visible - than all the other tuesdays, which would fit since the 7th of that year was a holiday. (Looking at the linked calendar type, the sundays and holidays appear to not have their font filled with color.)
I think it’s the same brand of calendar because if you see in the divider between the picture and the date, there’s what looks like a space where the subtitle of the picture is. Check that against the picture of the 1954 calendar I linked above.
The picture of the cowboy catching the horse is called “Turning A Stray.” I can barely make out the letters “Howa***” at the bottom right as the artist’s signature. However, searching a bit, I find this entry in the copyright archives attributing a 1953 picture called “Turning a stray” to one H. Relnhold. I’ll extemporate the Howa into Howard. Since the 1954 picture and 1956 are probably by the same artist, if we can find some sort of portfolio we only have to nail the skyline in the original picture and hope that’s attributed to the calendar in some way.
