From the 1850s to the 1960s the district was the center of commercial life in Waupun and was occupied by a variety of thriving businesses including dry goods stores, groceries, barbers, liveries, theaters, restaurants, taverns, and pharmacies, with office space and meeting halls occupying second and third floor spaces. The district is identifiable by the largely uninterrupted block of masonry commercial buildings facing the primary right-of-way in the small city and is Waupun’s most architecturally intact historic commercial area representing styles that include: Front Gabled, Commercial Vernacular, Italianate, Queen Anne, Neoclassical, Twentieth Century Commercial, Contemporary, and International styles.

The dense collection of commercial resources is a cohesive identifiable place representing a historic streetscape along East Main Street, a common historic arrangement in small cities and towns across Wisconsin. East Main Street historically served as the ‘main’ street and commercial destination in Waupun and still does to some degree. The area was primarily occupied by thriving commercial businesses that provided a wide range of goods and services to the City of Waupun and the surrounding area demonstrating the evolution of the community from a growing settlement frontier town, to an agricultural and industrial small city, to a more diffuse modern community. The buildings within the Waupun Commercial Historic District are relatively well preserved, maintain architectural integrity, and have much the same appearance today as they would have years ago.