Robert Hall Chilton was born in Virginia in 1817 and graduated from West Point in 1837. His military career took him west; repeatedly across the Santa Fe Trail. After distinguishing himself in the Mexican War he became a major of dragoons stationed at Fort Leavenworth and assigned to protect the Santa Fe Trail.
His role as a military leader on the trail required him and his men to safely manage trail traffic and protection of goods carried the length of the Santa Fe Trail. This involved protecting trade goods bound for Santa Fe as well as military supplies. Increased need for his military force occurred as part of hasty westward traffic caused by the California gold rush and times of unrest between trail travelers and American Indians.
Chilton protected the traffic along the trail for eight years. He resigned from the US Army at the start of the Civil War. He rose to Adjutant General and Chief of Staff to Confederate General Robert E. Lee.