One of the more fascinating figures during the Civil War was Miss Olivia Floyd. In early childhood, she broke her back and remained crippled her entire life. However, this burden did not stop her from getting involved assisting the Confederacy, where she served as an agent and messenger.

Miss Olivia Floyd

One of the more fascinating figures during the Civil War was Miss Olivia Floyd. She lived at a plantation house known as Rose Hill in Charles County Maryland (not to be confused with Rose Hill Manor in Frederick Country, Maryland). Rose Hill was built in 1730, and was the former home of Dr. Gustavus Richard Brown, a physician to George Washington. In later years Rose Hill was purchased by Ignatius Semmes, who later willed it to Olivia, her sister Mary and their brother Robert Semmes, in 1843.

In early childhood, Olivia broke her back, and remained crippled her entire life as a result of the break having never been set properly. But, this burden did not stop her from getting involved assisting the Confederacy during the war. Within a short time after the war began, Floyd became an agent and messenger for the South. On March 17, 1863, at the Battle of Kelly's Ford, while fighting as a member of J.E.B. Stuart's cavalry, her brother Robert was seriously wounded. He never recovered from his wounds, and died on April 3, 1863 at the residence of a Dr. Cooper in Fauquier County, Virginia at the age of thirty-four. Following his death, Floyd became an ever more impassioned supporter of the Confederate cause. As a means of concealing money and documents for her duties as a messenger, she used a wooden boat model that her brother Robert had made.

During the fall of 1864, in October, Colonel Bennett H. Young and twenty other Confederate soldiers made a successful raid on the town of St. Albans, Vermont. Following their raid, Young and his men escaped with the stolen money and horses, making their way into Canada. Once there, they were arrested by Canadian authorities. Upon learning of their capture, the Union officials sought their extradition for the purpose of placing them on trial on the grounds that they were spies. Young and his men were in fact Confederate soldiers who had escaped from a Union prisoner-of-war camp earlier. The Canadian officials refused to extradite them on the grounds that they were soldiers acting on official orders, however, their lives depended on being able to prove they were soldiers.

In furtherance of this proof, a message was started in the South requesting a copy of their commissions. This message passed from hand-to-hand, from Southern sympathizer to sympathizer, all the way from Canada to the state of Maryland. Here at Charles County, it finally reached Olivia Floyd, who was the last person in the chain of communications into Confederate territory.

However, the Union troops were suspicious of Miss Floyd, and just when she had received this message, Union soldiers were on their way to Rose Hill to search it. Looking for a place to hide the message, she thought of the pair of brass andirons, remembering that the brass balls at the top were hollow. She immediately placed the message in one of the hollow balls, not long before the Union soldiers arrived. Once there, the union soldiers searched the house, and finding nothing, stopped in the parlor to sit and relax for a short time by the fire, resting their feet on the very andirons that contained the message. Once the soldiers had gone, Olivia then retrieved the message, and hiding it in her hair, left Rose Hill. She soon arrived at the signal station at Popes Creek, Virginia where the message was then sent to Richmond. The authorities there received the message in time to forward the commissions for Young and his men in time to save their lives.

Many years after the war ended, Olivia was invited to attend a Confederate Reunion held in Louisville, Kentucky as a personal guest of Colonel Bennet Young. With the help of a man named Adrian Posey, she was able to attend the reunion. At the gathering, Olivia was treated as an honored guest. Prior to this reunion, but after the war ended, Olivia Floyd sent the boat model and the andirons that she used to hide the many messages to Colonel Young.

Olivia Floyd died at Rose Hill.

Copyright © 1993-2022 by John T. Marck. All Rights Reserved. This article and their accompanying pictures, photographs, and line art, may not be resold, reprinted, or redistributed for compensation of any kind without prior written permission from the author.