As with nearby Anamosa, Monticello was located south of the Maquoketa River. The initial grid plat of 1850–1851 was oriented so that Main Street was on a north-northeast by south-southwest line; later additions went in a variety of other directions, including a railroad addition that simply paralleled the tracks (which ran in a north-northwest by south-southeast direction). The Dubuque and Southwestern Railroad was completed through the community in 1859. It was later met by the Davenport and Saint Paul Railroad at the south edge of town.
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