Evansville was first settled in the 1830s by New Englanders who were attracted to the area by its pristine wooded landscape and the placid Allen Creek. By 1855, the city recorded its first plat and was complete with homes, shops, and churches. Evansville is named for Dr. John M. Evans, a doctor and postmaster during the city's early years.
In 1863, the Chicago and North Western Railway came to Evansville, accelerating growth. At this point, Evansville's economy was based on industry and manufacturing of carriages, wagons, pumps, windmills and iron castings. The economy was also based on agriculture: dairying; farming (production of wheat and tobacco; and stock raising.
By the turn of the twentieth century Evansville had over 1900 residents, and by the 1920s, most of the buildings in Evansville's future Historic District were completed.
On November 11, 1918, Armistice Day activities celebrating the end of World War I took an ugly turn as some Evansville citizens began rounding up townspeople who they had deemed insufficiently supportive of the war, mainly due to their refusal or inability to buy war bonds. A German minister and his wife were apprehended on their way out of town before being brought downtown and forced to kiss the American flag. Other "slackers" were made to wear sleighbells as they rode atop a car's radiator, while others were forced to dance in a snake formation around a bonfire. A 73-year-old woman who passed on participating in the "Your Share is Fair" war bond campaign was dragged from her home by the mob, placed in a large animal cage and paraded about the streets before being parked before the fire. The woman, Mary J. Shaw, had previously bought bonds and supported the Red Cross and other war relief efforts. After refusing to salute or kiss the flag she was rescued by other citizens. Her attempts to see her assailants punished were brushed aside by the local sheriff, and testimony before the state legislature was similarly disregarded.
The Evansville Historic District, which surrounds Main Street and stretches to the side streets of Garfield Avenue and Liberty Street, includes dozens of historic homes and other structures. The Wisconsin Historical Society called Evansville home to "the finest collection of 1840s to 1915 architecture of any small town in Wisconsin".
The Eager Free Public Library building was built with the bequest of a leading citizen, Almeron Eager, in 1908. Designed by the architectural firm of Claude and Starck of Madison, Wisconsin in the Prairie style, it features stained glass windows and plaster friezes just below the overhanging roof line. A 1994 addition at the rear of the original building was designed to match the original architecture, while adding much needed space and handicapped accessibility. The intersection on which the library stands also contains a Greek Revival home (now a funeral parlor), a High Victorian Gothic brick home (now housing the local Masonic Temple) and a classic Victorian "Painted Lady" home, still a private residence.
The Evansville Seminary was located near College Drive in the district. Its building was designed by architect August Kutzbock.
In 1978, the historic district was placed on the National Register of Historic Places.