Kiddieland Amusement Park, near Chicago, had a ride called the Little Dipper, and those cool rockets with the guns too. I wonder if that's where the pictures were taken. Boats are also listed as an attraction that opened there in 1949, but I didn't see a picture of them in the Wikipedia article.
That's entirely possible. I haven't really narrowed down exactly where these folks lived. "Ray and Dad" went on hunting trips to Wyoming. That's only a couple states west of Illinois...