Bert and Mary Cunningham built a round barn on their forty acre farm near the city of Viroqua, Vernon County in 1915. The barn's unique design included an arrangement of stables, pens, and cow stanchions around the perimeter of the lower floor as well as a milking facility. The upper level was hay storage and a large silo is located at the center of the interior. Round barns were part of an exploratory movement in dairy farming around the turn of the twentieth century which focused on efficiencies in physical labor. Bert Cunningham may have been drawn to these ideas, having limited physical abilities due to an accident earlier in his life.

Centric barn building in Wisconsin began in the late 1800s, but true round barns are seen after 1900. Round barns are an expression of a progressive approach to farming that included emphasis on efficiency. The Cunningham barn is a rare and highly intact example, having added distinction due to its roof truss structure and hollow structural clay tile wall construction. The design and construction of this barn is attributed to Alga Shivers, the son of a slave and a noted local builder of vernacular round barns in Vernon and Monroe Counties in the early twentieth century. Shivers recognized barn designs are, without known exception, constructed of wood. The roof construction of the Cunningham barn, emphasizing the efficient pattern of roofing boards and the utilization of a full-length truss spanning from sill to the central peak creating a gambrel shaped roof, resembles that of other local round barns known to have been constructed by Shivers. While it cannot be substantiated that Alga Shivers designed and built the Cunningham round barn, it is attributed to him.

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