This mission was special for Harriet, not just because she wanted her brothers to be free but because they were to be sold on the steps of the courthouse in Cambridge the day after Christmas in 1854.

Sentiments in Dorchester were divided on the sale of slaves at a time when the Dorchester County Courthouse served as the center for the largest slave market on the Eastern Shore. This attracted the attentions of slave traders from other regions, including the Woolfolk brothers, Baltimore slave traders who opened an office in Cambridge.

Some Dorchester slave owners opted to sell their slaves through slave dealers instead of having their neighbors and friends see them sell their slaves at auction. Slave dealers were instructed to come at night to carry away the slaves to be sold. Slaves and neighbors were told the slaves had escaped.

Another aspect of the slave trade which encouraged support of the Underground Railroad among white residents in Dorchester were scenes of distraught black people being sent away from their home and families. The sight of large slave coffles (groups of men, women and children chained together) trudging off to Baltimore overland or via boat from Cambridge was distasteful and uncomfortable to some Eastern Shore whites.

When Harriet’s brother, Henry, was interviewed in Canada in 1863, he tells of “a white gentleman who offered to buy us,” after learning that the slaveowner, Eliza Brodess intended to sell the three brothers. But “after the gentleman saw she wouldn’t sell us to him at any price, he sent us word, ‘Boys, I can’t buy you. If you can get away, get away.'”

In addition to the negative reaction to slave trading, Harriet Tubman also received help in Dorchester to lead slaves to freedom from black watermen she knew as well as farmers and timberland owners throughout the region who had hired her and her team of oxen. And the institution of slavery in Dorchester also had created an extensive network of connections between black and white families which Tubman used to her advantage.

By 1854, Eliza Brodess was a widow. Her late husband, Edward, already had sold some of the slaves he had inherited and their offspring.  The widow Brodess faced a large debt and had a large family to care for as she considered what to do with the three Ross brothers, who already had attempted previous escapes.

The decision was made to sell the brothers on the steps of the Dorchester County Courthouse. The auction was set for Dec. 26, 1854.

When Harriet learned of the fate facing her brothers, she sent word to them through a freed black, Jacob Jackson. Realizing the letter would be read at the Post Office in Woolford, as required by law, Tubman wrote in code “tell my brothers to be always watching unto prayer and when the good old ship of Zion comes along, to be ready to step on board.”

Confronted with the letter by community officials, Jackson pretended to be confused. But he passed the message along to the three Ross brothers.

Three others joined the Ross brothers on their flight to freedom that long ago Christmas Eve. Among them was Jane Kane, Ben Ross’ fiance. She dressed as a man to steal away from the farm of her owner, Horatio Jones, which was also located in the Harrisville/Peters Neck area.

As one brother took steps toward starting a new family, another left his family behind after staying behind while his wife, Mary, gave birth to their third child.

Robert Ross realized he could not avoid being separated from his family.

If he chose to stay in Dorchester County, he would be sold the day after Christmas. Through escape he could gain freedom.

Falling in winter, when there was far less to be done on farms, the Christmas holidays were a time when many allowed their slaves to travel to visit family. This created a good opportunity to escape, providing a few days distance before a search would begin.

That Christmas, when the three brothers went to visit their parents, Ben and Rit Ross at Poplar Neck near Choptank in Caroline, the plan was underway.

Ben Ross Sr. and his four adult children made a decision that day to keep Rit in the dark about the escape that was in the works. Years later, they talked about this decision by describing how they were worried that Rit would not be able to keep her emotions in check. They thought she might raise such an all-out ruckus of grief over this unexpected farewell that it would draw unwanted attention to the cabin.

Tubman and the brothers hid from her in a little outbuilding that served as a corncrib. There, they watched through a crack in the door while their mother prepared the Christmas dinner they would not be sitting down to eat.

Perhaps Ben, Tubman, and the brothers were worried, too, about whether Rit would hold up under questioning once the brothers’ owner alerted local authorities that Robert, Ben, and Henry had gone missing.

After all, Ben was worried about his own ability to deal with those questions. He put on a blindfold that Christmas Eve every time he came near Harriet and the brothers. He kept it on even though he hadn’t seen his daughter Harriet in five years and didn’t remove the blindfold even as he followed his children for several miles after they left his home.

Ben Ross Sr. kept the blindfold on until he had to let his offspring continue on their way. Then he waited until he could no longer hear their footsteps before he took the blindfold off. This way, when authorities came to ask if he’d seen his children, Ben Ross Sr. could honestly say that, no, he had not seen his children. Those investigators did show up asking their questions soon enough. And in response, Ben told them the truth: He hadn’t seen his sons at all around Christmastime.

William Still’s records show the group arriving Dec. 29, 1854 in Philadelphia. Among the expenditures he lists in January is the purchase of new shoes for the runaways. From Philadelphia they eventually traveled to Canada, where they began new lives in freedom.