The Litchfield and Madison was incorporated on March 1, 1900 by James Duncan to take over an isolated line of the Chicago, Peoria and St. Louis Railroad between Litchfield, Illinois and Madison, Illinois.
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In 1889-1890, the Chicago, Peoria and St. Louis Railroad began constructing a railroad line at Winston, Illinois, about a mile from Litchfield, Illinois, with the intent of the line eventually reaching Madison, Illinois.
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