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Little evidence remains, but Monona was once connected to Madison by an interurban trolley. Popular in the first two decades of the 20th century, many lines were proposed and mapped out for the interurban lines. During this same period the Madison Interurban and Traction Company attempted to promote an interurban service around Lake Monona for owners of summer homes and cottages. Advertisements compared the intended routes to that of the Michigan Traction Company, which serviced Chicago's North Shore residents. In 1912 $40,000 was received from Monona property owners who subscribed to the installation of the line. By 1913, tracks were laid on the side of the narrow dirt road, which is now Monona Drive, from Fair Oaks and Atwood Avenue, and extended approximately as far as Spring Haven, presently Winnequah Road. The interurban trolley was in use for only about one year. During WWI, funds to continue the system were diverted and its maintenance was neglected. The trolley cars lay on a section of unused tracks until approximately 1924.

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