Madonna Trail
Madonna of the Trail
The Madonna of the Trail monuments were placed by the Daughters of the American Revolution between 1928 and 1929 to honor the spirit and sacrifice of the pioneer women who helped settle the American West. The monuments were placed along the National Old Trails Road, also known as the Ocean-to-Ocean Highway, which later became parts of U.S. Highway 40 and Route 66.
There are 12 Madonna of the Trail monuments located from Maryland to California, with one monument in each state along the historic route. Together, they represent the coast-to-coast journey of the early pioneers and the determination and courage of the families who traveled west.
Sculptor August Leimbach described the monument as a tribute to the pioneer mother — a woman strong and brave, protecting her children and family in an unknown and often dangerous land — symbolizing the courage and sacrifice of the women who helped shape the nation.
The Challenge — Sea to Shining Sea
This challenge is to visit and photograph all 12 Madonna of the Trail monuments during the current rally season, between April 1 and October 31.
Photo Requirements
Each submission must include:
- The Madonna of the Trail monument
- Your motorcycle
- Rider flag (and passenger if applicable)
- Enough background to identify the location or a geotag-enabled photo
If the motorcycle cannot be included in the same photo, submit a second photo showing the motorcycle and rally flag in nearby designated parking.
GPX File
- Revised April 2026