Centered around Main Street, which parallels the Milwaukee River, West Bend’s historic downtown commercial business district is approximately four blocks long. While city commerce began in the 1850s, the district’s earliest extant building dates to the 1860s. As the city was founded based on its mid-point location between Milwaukee and Fond du Lac, the district provided not only the standard goods and services required by the growing community, but also offered a variety of lodgings for weary travelers. While commercial offerings have changed over the years, and despite modern shopping development on the outskirts of the city, the downtown district, with its restaurants, taverns, specialty shops, hardware store and restored theatre, continues to thrive.

In addition to its commercial significance, the district’s seventy buildings exhibit most of the architectural styles popular in Wisconsin between the 1860s and 1970s, including (but not limited to) Italianate, Queen Anne, German Renaissance Revival, Classical Revival, Period Revival and 1940s-1960s Contemporary examples. Furthermore, a good number of the buildings were designed by such well-known Wisconsin architects including Leigh Hunt, Roger Sutherland and Van Ryn & DeGelleke, as well as those known regionally or nationwide, such as Graven & Mayger and Louis A. Simon.