Duane Beckett
When it comes to American Civil War history, prison escapes often sound like unbelievable plots in bad books or even worse movies. From tunnel mazes to prisoners remembering complex mazes of corridors, to soldiers surviving extreme weather in nothing but prison clothing, these stories are hard to believe.
Amazingly, the following strange Civil War prison escapes are real. They weren’t always clean getaways with perfect endings, but they were real attempts made by desperate soldiers.
Libby Prison’s “Rat Hell” Tunnel Stampede
Libby Prison in Richmond, Virginia, held Union officers, and in February 1864, Colonel Thomas E. Rose helped lead one of the war’s wildest breakouts. The National Park Service reported that 109 prisoners fled Libby on the night of February 9, 1864, with 59 reaching Union lines.
They did it by going below the prison into a filthy basement area known as “Rat Hell,” then digging a tunnel toward a nearby warehouse. History.co.uk reported that more than 100 Union soldiers escaped through that tunnel into the winter night.
I love a good prison-break story, but this one is hard to believe, even though it’s true. A supposedly secure Confederate prison was beaten by men willing to face a rat-infested basement.
Point Lookout’s DIY Chesapeake Bay “Fleet”
Point Lookout Prison Camp in Maryland held Confederate prisoners, and its location made escape tempting but unlikely. It sat where the Potomac River meets the Chesapeake Bay, with water everywhere and Union patrols close by. Maryland’s Department of Natural Resources states that Point Lookout was isolated enough to make escape difficult.
Fold3 reported that Confederate prisoner Simon Seward studied guard movements, slipped past a fence, ran under fire, and threw himself into the Chesapeake Bay before making his way south.
Another account in Between the Lines mentioned two escaped Point Lookout Confederate officers, Bruce and Howell, who were in a poor little yawl during a southern run in June 1864. Crossing guarded wartime water in anything that floated feels hard to believe, but it really happened.
Florence Stockade’s Night-Perimeter Slip
Florence Stockade in South Carolina became a Confederate prison for Union soldiers in late 1864, after many prisoners were moved away from Andersonville. One escape involved Union prisoners from the Plymouth, North Carolina, capture group.
The Civil War Plymouth Pilgrims Descendants Society records that several men escaped from Florence Stockade on October 7, 1864, after Private Goe bribed a guard with a gold watch. The group included Reed G. Beggs, Norval D. Goe, John F. Rupert, James S. Cooper, and George Shaffer, though they were later discovered and taken back.
This one doesn’t need a tunnel or a fake uniform. A gold watch was the key, but it’s also the part that sounds made up. Where did that watch come from?
Castle Thunder’s Corridor-Maze Escape
Castle Thunder was a notorious Richmond prison complex tied to warehouses, deserters, civilian prisoners, and Union captives. Encyclopedia Virginia states that it was one of the prisons operating in Confederate Richmond during the war.
Civil War Richmond highlights a January 16, 1864, escape from the prison opposite Castle Thunder. Eighteen Yankee deserters escaped by cutting through a wall into an adjacent commissary warehouse.
The event sounds like a cut scene from a video game, but this was real. Men in a guarded Richmond prison cut through a wall, crossed into another warehouse, and vanished into the city’s wartime maze.
Elmira Prison’s Tunnel Breakout
Elmira Prison Camp in New York held Confederate prisoners, and the weather alone could break a man. The better-documented escape here wasn’t a clean river run; it was a tunnel breakout during the Civil War.
The Chemung County Historical Society found that Washington D. Traweek, Berry Benson, and other Confederates escaped through a tunnel discovered missing at roll call on October 7, 1864. Rumors inside the camp got wild, with one prisoner claiming 25 men had escaped with stolen horses.
Information from the Chemung County Historical Society also shows Elmira had other bizarre escapes, including a man named Buttons who faked his own death and jumped from a coffin on the way to the cemetery.
That’s the hard-to-believe part. Elmira wasn’t just cold and deadly; it produced strange Civil War prison escapes that sound like someone added a Hollywood twist.