On the Road to Freedom Day
May 24, 2021

On the road to Freedom Day, many black families left the South following the Emancipation Proclamation. They preferred being together under the Union Army’s protection rather than staying on the farms and plantations as slaves. Three slaves escaped from Sewells Point from the Confederate Army using a small boat and found haven at the Union stronghold at Fort Monroe in Virginia, known as the “Freedom’s Fortress.”

At Fort Monroe, General Benjamin Butler refused to comply with the Fugitive Slave Law and protected these three escaped slaves by classifying them as contrabands of war. This classification meant that the Union Army could seize any slaves being used to support the Confederate rebellion. The passage of the Civil War Confiscation Acts of 1861 and 1862 made it legal to seize slaves, and the 1862 act authorized the federal government to free slaves in conquered rebel territory. As the Union Army continued its successes, more and more self-liberated contrabands moved from slavery to freedom toward Union camps.

Even the defeat of the Union Army at the Second Battle of Bull Run did not stop blacks from following the Union Army. Photographer Timothy O’Sullivan took a series of photographs in August 1862, where slaves were emancipating themselves with loaded wagons by fording the Rappahannock River in Virginia. That day, Union General John Pope’s Army of Virginia was in full retreat, falling back from the Rapidan River to a new line behind the Rappahannock River. Slaves saw the Yankee’s departure as their last chance for freedom and flooded North with the Union Army.

This image captures the hugely significant act in progress, slaves emancipating themselves on the road to Freedom Day.

Envisioning Emancipation, by Deborah Willis and Barbara Krauthamer, Published by Temple University, 2013

On Juneteenth, by Annette Gordon-Reed, Liveright Publishing Co., 2021