These blotters from the Dale Hastin collection aren’t dated, but most seem to be from before 1900. PDFs of the blotters are about 500 to 700 KB in size.
This blotter shows the Dakota territory, suggesting it is from before November 2, 1889, when the territory was split into the states of North and South Dakota. The blotter advertises diners, which C&NW introduced in 1869, and Palace sleeping cars, which C&NW introduced in 1877. So it is probably from the 1880s.
The Chicago, St. Paul, Minneapolis and Omaha was created in 1880, and by 1882 was taken over by the Chicago & North Western. However, C&NW ran it as a separate railroad for many years after that. Still, I’d date this blotter to the 1880s or 1890s.
Googling J.M. Whitman’s name reveals that he was general manager of the Chicago & North Western from 1889 or earlier to 1899. The 1900 Official Railway Guide listed him as Fourth Vice President and W.A. Gardner was the general manager. So I’ll this blotter probably dates to the 1890s.
The Colorado Special was inaugurated on February 6, 1898 as a 28-hour train between Chicago and Denver, with C&NW/UP promising to reduce the time to 24 hours only if the Burlington Route offered a 24-hour train first. It continued to operate at least into the 1920s, but not into the 1930s. So this blotter could be from 1898 or 1899, but is is likely from the early twentieth century. Below is a postcard showing the train in 1907.