Many residents of this area were employed in the wagon or tobacco industries. When freight and passenger service between Stoughton and Milwaukee began in 1853, it ensured the success of these industries, although both had significant downturns in the 1920s. The T.G. Mandt Wagon Works were established in 1865. In 1889 the company reorganized as the Stoughton Wagon Company. T.G. Mandt began another wagon firm in 1896, which was sold to the Moline Plow Company after Mandt’s death in 1902. After the decline of the Stoughton wagon industry in the 1920s, new vehicle and part factories such as Highway Trailer and the Stoughton Cab and Body Company were established. Semi-truck trailer manufacture remains an important part of the local economy.

The weathered tobacco sheds of Jefferson, Rock and southern Dane counties are testament to this important industry in southeastern Wisconsin. Tobacco cultivation began near Edgerton in the 1850s, and the tobacco trade began in Stoughton about 1871. After harvesting, tobacco is cured in specially-designed sheds and then stored in warehouses before shipping. In Stoughton, the first warehouse was erected in 1877; by 1882 there were ten and by 1898 there were seventeen. (Three remain, at 515, 524, and 567 E. Main St.) By 1926, at least thirty tobacco firms had done business in the city. Many residents were involved in growing, harvesting, sorting and shipping; Severson, Bjoin, Halverson, and Holtan stand out among early individuals and families from the East Side Historic District area associated with tobacco.

The decline of the tobacco industry was evident in the 1920s, with soil depletion and poor crop yields in addition to less consumer demand. The industry rebounded by 1950. Today, tobacco remains a cash crop in the townships surrounding Stoughton.