Two large fires and a burst of economic development resulted in most of Darien’s downtown development, creating a compact and cohesive commercial streetscape. Major fires in 1909 and 1912 resulted in the construction of half of the buildings in the district. These red brick buildings, added to the other brick blocks constructed earlier, give Darien's downtown a distinctive appearance with a strong sense of time and place.

Darien's commercial area developed along Wisconsin Street after the railroad came to town in 1856. By 1890, the district was filled with wood buildings of various sizes and shapes. When local farmers entered a successful and profitable period from the late 1890s through 1920, Darien's merchants profited as well. Beginning in 1897, when the appropriately named Farmers State Bank constructed a brick building, to 1916, when the last large brick building was constructed in the district, Darien's downtown was transformed.