That's odd !! As far as the age,,except for the fairly new looking wood on that side support,, I see no reason they couldn`t be from that era !! The artwork looks correct as well as the aging of the paint that I can see !! The smaller object look to be part of a bean bag/ball toss game of some type !! I do not think these two things go together !!
By the time I was going to fairs ect ( 50`s) they were already obsolete !! So 30`s or 40`s is what I would expect !!