Wisconsin's first train wreck proved to be its worst. On the morning of November 1, 1859, a Chicago and North Western train jammed with residents of Oshkosh, Fond du Lac and other points on the northern end of the line hit a large ox which had jumped onto the tracks near Johnson Creek. The animal was caught up on the cow-catcher and carried about a dozen rods, when it fell under the locomotive just as it was crossing a small bridge. The engine was thrown into a ditch, the baggage car fell over into a pool of water and five passenger cars were driven together, "shattered, smashed up and demolished." 14 persons were killed, at least 30 injured. A cornnor's jury found the accident "unavoidable," but a cry was raised to make farmers responsible for the conduct of their livestock.

Another train disaster that made the headlines occurred near East Rio in the early hours of October 28, 1886. The Chicago, Milwaukee and St. Paul's limited train, rushing along at the rate of 40 miles an hour, hit an open switch. The train telescoped and the day coach burst into flames. Those in the sleeper escaped. The death toll has been variously estimated at from 11 to 17. The coroner's jury found that "said switch was left open by the negligence of C. H. Wells, an employee of the Chicago, Milwaukee and St. Paul Railway Company."

The worst 20th-century wreck involved a head-on crash between two interurban Milwaukee Rapid Transit and Steelrail Company trains near Milwaukee on September 2, 1950. 10 persons were killed, more than forty injured. The company's president, J. E. Maeder, was at the controls of one of the trains.

Other serious railroad disasters were those at Kenosha (June, 1864; 3 dead); near De Pere (June 24, 1900; 6 killed, over 60 injured); at Alma (May 30, 1902); near Janesville (February 11, 1906; 4 killed); near Waupaca (September 10, 1906; 2 killed). On November 15, 1907, a fast train at South Milwaukee struck a large crowd of workmen on the tracks, killing 6 and injuring others, of whom some died later.

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