At dusk on February 9, 1864, more than one hundred Union officers held in Richmond’s infamous Libby Prison were about to attempt what few had dared even to plan. With no prisoner exchanges taking place, escape had been discussed almost from the moment they arrived. A few men had already slipped past the guards dressed as civilians, claiming to be visitors. Another scheme involved digging a tunnel to the city sewers, but water seepage had doomed that project.

Now the prisoners had committed themselves to a far more ambitious plan, one that had taken thirty days of painstaking labor and brought them within inches of discovery. The man who recorded it all was Colonel Harrison Carroll Hobart of the Twenty-First Wisconsin Infantry, captured at Chickamauga and confined at Libby, who ten years later set down his account at the request of his friend Brigadier General John Beatty. The tunnel’s beginnings were modest. In the ground floor of the prison building sat a kitchen with a fireplace and stove used by the prisoners in the upper rooms to cook their food.

Below that lay a cellar, one room of which served as a storeroom. It was situated beneath the hospital and next to the street, and although not directly under the kitchen, its position allowed access by digging downward and back through the chimney construction. From that cellar room, the prisoners proposed to build a tunnel under the street to a point beneath a shed attached to a brick building on the opposite side. From there, they would emerge into the street disguised as civilians.

Only about twenty-five men were let in on the secret. The rest of the prison knew nothing until two or three days before the escape. The tools were crude: a table knife, a chisel, and a spittoon. They removed enough stone from the fireplace to allow a man to squeeze through a sloping opening into the cellar below, then began digging through the foundation wall toward the street.

Only two men could work at a time. One entered the hole with his tools and a small tallow candle, dragging behind him the spittoon tied to a string to collect the dirt. The other man ventilated the passage by waving his hat, using another line to pull the spittoon back once it was full, hiding the contents under straw and cellar refuse. Each morning before dawn the work crew returned to their rooms, carefully sealing the tunnel entrance and resetting the bricks in the chimney with practiced skill.

One error nearly ended the entire project. Believing they had dug far enough, the diggers began to work upward toward the surface. While the man inside felt his way cautiously, a small amount of surface soil suddenly caved in, and through the opening he saw two guards looking directly at him. One said to the other that he had been hearing strange noises in the ground there.

After listening for a moment, the other replied that it was only rats. The crew was not discovered. After consultation, the hole was carefully filled and reinforced. Work resumed, and after digging another fifteen feet, they reached the target point beneath the shed.

The tunnel ran eight feet below the street and stretched sixty to seventy feet in length. It was barely wide enough for an adult to crawl through, pushing and pulling with hands and feet. Among the officers credited with the work, Colonel Thomas E. Rose of Pennsylvania received special mention for his role in its completion.

Once everything was ready, the escapees organized themselves into two groups. The first was commanded by Major McDonald of Ohio; the second fell under Hobart’s supervision. Both groups had supplied themselves with civilian clothing, sent to the prison at various times by friends in the North, and had filled their pockets with bread and dried beef from their boxes. Around seven o’clock on the evening of February 9, the escape began.

McDonald’s team went first. To divert the guards, the prisoners staged an impromptu dance with music in the main room. Every man had to pass directly in front of the Confederate sentinels when stepping out into the street beyond the line, and the guards had orders to shoot any escaping prisoner, without even a command to halt. The first men to descend into the tunnel wore the quiet, solemn expression soldiers often have before battle.

The scene was strange and vivid: dancing on one side of the room, dark shadows disappearing through the chimney on the other, and the same shadows reappearing on the opposite sidewalk. The sentry, standing at his post, called out into the evening air, eight o’clock, post number one, and all is well, while a Northerner passed before him and a line of Northern soldiers crawled beneath his feet. The passage was so narrow that movement was slow. Each man advanced only a few inches at a time, and to make it easier, outer clothing was removed and pushed ahead.

By then the plan was known to the entire prison. As the first men reached the street and walked quietly away under the gaze of hundreds of fellow prisoners crowded at the windows, excitement swept through the building. Men rushed to the chimney, demanding their chance to escape. The organized groups had intended that no one else would leave until the following night, worried it would ruin their chances.

But the thought of freedom and fresh air, and the dread of remaining in the dark, foul prison, would not allow them to accept refusal. Major McDonald and Hobart conferred and agreed that the rope used to lower men into the cellar would be pulled up for one hour after the last members of the two groups had gone, and then left available to everyone in the prison. Hobart had joined his fate with Colonel T. S.

West of Wisconsin, and the two were among the last of the second group to crawl through the tunnel. Around nine o’clock they emerged, crossed an open yard cautiously to an arched passage, then stepped into the street and walked away slowly, as if engaged in serious conversation. Once beyond the reach of the guards’ rifles, they judged that the safest route was to turn and pass through one of Richmond’s main streets, reasoning that no one would suspect escaped prisoners of taking such a direction. With his pale face and long beard, Hobart took the arm of Colonel West and played the part of a feeble old man in very poor health, suffering from a severe tubercular cough.

In this guise they passed under the bright gaslights and through the crowded streets without drawing suspicion. They met police, squads of soldiers, and many others who looked at him with pity and moved out of his way because of his apparent physical frailty. Nearing the outskirts of town, they slipped into a ravine that allowed them to leave the city without passing through any of its streets. In the end, over one hundred officers and soldiers of the Union army escaped from Libby Prison through that tunnel.

Hobart’s account preserves not only the mechanics of the escape but the peril and tension of those final hours. The dance continued upstairs while men vanished below. The sentry’s voice rang out through the night, unaware of the silent line of men moving beneath his feet. For the prisoners, the tunnel was thirty days of cramped, dangerous labor that ended with a single night of freedom, or at least a chance at it.

For Hobart, it was a chapter he would recount years later at the request of a friend, ensuring that the story of what happened inside Libby Prison in February 1864 was not forgotten.