The Madonna of the Trail monument in Wheeling is one of the 12 such statues erected to honor America’s pioneering women. The National Society of the Daughters of the American Revolution commissioned the design and construction of the oversized statues, erected in 1928 and 1929 along the National Road from Maryland to California. Designed by sculptor August Leimbach, the Madonna statues feature a pioneer woman holding a baby with one arm and a rifle with the other. A small boy clutches her skirts. The figure itself is about 10 feet tall.

Dedicated on July 7, 1928, the Wheeling statue is on the edge of Wheeling Park, facing the National Road. The Wheeling chapter of the Daughters of the American Revolution has maintained a light on the Madonna since 1928. In 2013, the Wheeling statue was restored for the first time since its dedication.