We’ve seen the cover of this children’s menu before, and on the PDF page I dated that one to 1933. I based that date on the Union Pacific’s web page saying that it last used the “Overland Route” logo in 1933, but it is possible that it continued using it on menus for a few years more.
This menu appears to be older than the previous one, as it has lower prices. The previous menu had breakfasts for 40¢, 60¢, 75¢, and $1, while this one has breakfasts for 40¢, 50¢, and 55¢. The 40¢ breakfasts are roughly comparable, but the 55¢ breakfast on this one is comparable to the $1 breakfast on the previous one. Unlike the previous bear menu, the current one doesn’t offer pancakes, waffles, or French toast, but it does have an a la carte section that includes fruit, juices, cereal, or an egg, all for 15¢ each. If the previous menu is truly from 1933, this one must be from the 1920s.
Here’s another version of the same menu that, judging from the prices (60¢, 75¢, and 85¢) and the non-Overland Route logo, was issued after both the above menu and the one posted earlier. The menus sides of all of these menus are illustrated with scenes from Goldilocks and the Three Bears, but this one, unlike the earlier versions, attempts to tie in to Yellowstone with the words, “The playful bears always delight visitors/Yellowstone Park.” This message conflicted with the drawings, one of which shows Goldilocks running from the bears in fright.