The greater Stoughton area was hunted and trapped by the Ho-Chunk Nation and other Native American tribes through the 1700s. Surveyed in 1833, the area was described as timbered and carpeted with prairie along the Catfish River, later renamed the Yahara. Luke Stoughton came to the area, recognized its potential for sawmills and gristmills, and purchased 800 acres in 1847, opening it for settlement. By 1853, land he donated enabled the railroad to pass through the community, bringing passengers and service. Farmers brought wheat to Stoughton for grinding, which encouraged T.G. Mandt, a Norwegian, to build a wagon factory in 1865 that employed over 200 Norwegians. Later, tobacco provided work for many new residents, mostly Norwegians. With the wagon factory, tobacco industry, and railroad, Stoughton's economy flourished, and by the turn of the century it was a major economic center in southern Wisconsin. Cut lumber from surrounding lands was used to build the first generation of Main Street buildings, including an early general merchandise store at Main and Division Streets in 1847 and an inn soon afterward. Between the mid-1880s and 1904, seventy-six business buildings were erected on Main Street from the Yahara River to the railroad tracks. Stoughton gained a reputation as first in commercial importance in Dane County, serving Dane and Rock counties with extensive retail, financial, and professional services. The district reflects those historic uses through diverse buildings and streetscapes, including an architecturally significant collection of Victorian and early twentieth-century commercial buildings ranging from Italianate to Beaux Arts, many of which retain a high degree of integrity and their original exterior materials and features.