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Woodworth arrived in Chicago in 1833, the first year of its incorporation as a city in Cook County, when its population totaled 500.
He immediately began operating a dry goods business which continued until 1840.
In 1835, while operating his dry goods business, he applied for, and received, wharfing privileges.
He eventually contracted to work on the construction of the Illinois and Michigan Canal.
He briefly left Chicago for Marseilles, LaSalle County, Illinois, to oversee his interest in saw-mills ; the Marseilles mills were considered among the most advanced mills of their time.
He returned to Chicago in 1842 when the mills were destroyed in a fire.
His business endeavors in this period sometimes included other business partners such as one of his brothers, Dr. Robert P. Woodworth.
After he returned from LaSalle County he purchased a flouring milling operation that was connected to the pumps and reservoirs of the Chicago Hydraulic Co.
He was invited at various times to serve the community in a series of elected political offices.

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