There was a dubious tradition in Ye Olden Days to depict Houston as a place with rolling hills, and not as a flat swamp with occasional buildings. The above picture is one example.
However, the rollercoaster in the prairie feels right. Maybe the long-gone Luna Park on White Oak Bayou?
Normally, I'm a total stickler for image sources, but I can't recall if I found these two at The Library of Congress and/or University of Houston Digital Library.