National DAR Commission chairperson Arlene B. Nichols Moss and her artist son worked with architectural sculptor August Leimbach to design the DAR statues. Sculptor August Leimbach envisioned a scene in which she is looking for her husband whom she believes to be in danger.
Each Madonna of the Trail strides purposely westward, dressed in a simple homespun prairie-style gown and wide-brimmed sunbonnet. Like other Pioneer Mother statues erected during the late 1920s, the 12 DAR statues balanced strong, active roles for women with softer maternal symbolism.
The statues were cast from algonite (a form of cast stone produced from a mixture of crushed marble, Missouri granite, stone, cement and lead ore) at the cost of $1,000 per statue. The statues were placed along key white migration routes, such as the early-19th-century National Road (later U.S. Route 40) and Santa Fe Trail (later the infamous Route 66). But the precise location of the monument within each state was selected based on both the site’s historical significance and the influence of local DAR and National Old Trails Association chapters.
The DAR chapters competed for the Indiana Madonna of the Trail: Richmond, Indianapolis, and Terre Haute. The statue was placed at the entrance to Richmond's Glen Miller Park, near the site of the first National Road toll gate in Indiana. National DAR chair Mrs. John Trigg Moss spoke at its dedication on October 28, 1928.