At the western end of the National Old Trails Highway, the Madonna of the Trail in Upland, California, stands as one of twelve monuments placed across the country. Dedicated in 1929, the series was commissioned by the National Society of the Daughters of the American Revolution (NSDAR) to honor the strength and perseverance of the pioneer women who helped guide America’s westward growth.
The statues were created by sculptor August Leimbach, inspired by Portland’s Sacagawea monument. Each figure stands about 10 feet tall, weighs five tons, and depicts a pioneer mother striding forward with a rifle in hand, a child at her side, and another in her arms. The Upland Madonna is said to represent several historic routes, including the Mojave Trail, the de Anza Trail, the Emigrant Trail, and Canyon Road.

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Though originally planned for San Bernardino, the monument ultimately found its home in Upland and was unveiled on February 1, 1929, as the 11th in the series. Over the years it has endured challenges, including a falling tree in 1957 and earthquake damage in 1991, but careful restoration has kept it standing.
The Upland Madonna not only honors pioneer mothers but also marks the western end of the National Old Trails Highway, a road that laid the groundwork for Route 66. With only two Madonnas located along the Mother Road—this one in Upland and another in Albuquerque—it remains a distinctive stop for Route 66 travelers.