Early Business Career
Woodworth began his career by helping his older brother run the family farm in Washington County, NY. When Woodworth was 19 his brother arranged the exchange of the family farm in Washington County, NY for a farm in Onondaga County, NY. He continued to work on the new family farm in Onondaga County, NY for his brother until he was 21. In his last two years of farming in Onondaga County, we worked to clear land and erect buildings on a tract of land known at the time as the "Indian Reservation."
Upon leaving farming, he struck out initially to run a dry goods business. Despite his limited education, he became a school teacher in the local school district of Fabius, New York. In 1826 he was appointed inspector of the common schools. He briefly considered a career as a physician while working for another brother, Dr Robert P. Woodworth. In 1827 he decided to work along the Erie Canal. There he and another Woodworth brother operated a small scale dry goods or trading business and lived in Erie, Pennsylvania. From 1829 to 1832 he served as a justice of the peace in Pennsylvania.
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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