As shipbuilding along the Medomak River declined in the late 1880s, Waldoboro sought new industries to support its economy. In 1888, the town heavily invested in constructing the Waldoboro Shoe Factory, covering most of the $32,000 cost. The four-story, 30,000-square-foot building operated using gasoline engines and a system of belts and pulleys, as electricity was not yet available. Although the factory was designed to support the local workforce, it only produced shoes for a short time before becoming vacant.

The building remained unused until 1920, when the Holub, Dusha Company repurposed it for manufacturing button machinery parts. This marked the beginning of a new era for the site. In 1921, the Paragon Button Corporation began making pearl buttons from imported shells. The company grew to employ about 82 people in Waldoboro and contributed to the town's industrial base for decades. This operation continued under new ownership after Stanley and Rolsala Gerson of Patrician Plastics purchased the facility in 1943.

Under the Gersons, the factory transitioned from pearl to plastic button production in 1957. By 1981, the workforce had declined to just 25–30 employees, but they still produced large quantities of buttons, dice, dominoes, and poker chips. The factory eventually closed in the early 1980s, and since then, the historic building has not housed any formal businesses, reflecting the broader industrial shifts that shaped Waldoboro's economic history.