A three building complex that began as a tobacco shipping plant; During the civil war, it housed Union army prisoners. Historically, it was ideal for a prison, but was plagued by over population and food shortages. It has since became known for the 'Libby Prison Tunnel escape. 109 prisoners escaped with 59 eventually reaching Union lines. Judson Kilpatrick hosted a disastrous rescue attempt which led officials to threaten to destroy the facility with mines.

Libby Prison was a confederacy prison in operation from 1862-1895. It began as a tobacco housing and shipping plant built by John Enders Sr, who was killed during construction of one of the buildings. Once the civil war began, the family of John Enders began leasing off parts of the building to use as a prison for the confederacy. Following the first battle of Manassas, union prisoners were starting to overpopulate. The prisoners were being held in a prison depot, but its location made it difficult to secure. 
 It was a desirable location compared to the old prison depot at Main and 25th streets. Almost immediately after its conversion, news of overcrowding and food shortages about the prison began to be published.  
The prison became known for the 109 union officer escape on Feb 9, 1864. After tunneling for more than sixty feet, they escaped. Eventually, 59 of the original 109 made it to union lines. Major General H. Judson Kilpatrick led am ambitious raid on the prison from late February to early March. It failed, and prison officials began to place mines under and around the prison, threatening to detonate them if any more action was taken.

Zombek, A. M. Libby Prison. (2014, January 23). In Encyclopedia Virginia. Retrieved from http://www.EncyclopediaVirginia.org/Libby_Prison.