One of the best aspects of working on our new section on the American Revolution in Virginia is the opportunity to learn about lesser-known events that reflect the complexity of freedom stories in the Commonwealth during the Revolutionary period. One of these overlooked stories is the Great Willoughby Slave Escape, as detailed in our new entry by Ervin L. Jordan Jr. 

On a Sunday night in mid-April 1776, eighty-seven people enslaved by Colonel John Willoughby Sr. on Willoughby Point—a narrow finger of land reaching into the Chesapeake Bay that had been in the Willoughby family for as long as Virginia had been a royal colony—made their way to the shoreline. There, they boarded an improvised fleet of barges and boats and departed under a crescent moon across Willoughby Bay to a British flotilla moored there. Once safely aboard, they took advantage of the emancipation proclamation issued by Virginia’s last royal governor, John Murray, fourth earl of Dunmore, that offered freedom to those who would join the effort to put down the colonial rebellion. Fifteen formerly enslaved men from Willoughby joined Dunmore’s Ethiopian Regiment, the all-Black regiment he organized to join his forces.

The escape was extraordinary both for the degree of coordination it entailed—Jordan notes that the freedom seekers may have been aided by a covert coalition of British officers and white Virginians—and the fact that Willoughby’s entire enslaved population fled together in “one of the few instances of the large-scale liberation of a plantation’s workforce.” Escaping that night were fifty children, twenty-one women, and sixteen men between the ages of sixteen and sixty. 

In addition to one of the largest group escapes of enslaved people in Revolutionary Virginia, the Willoughby escape is also a poignant reminder that for many enslaved people, freedom during the American Revolution meant running toward the British and away from their Patriot enslavers. And some eighty-five years later, Fort Monroe, just across the channel from Willoughby Point, would serve a similar role for enslaved people seeking freedom behind Union lines.

By the time Dunmore’s fleet sailed from Virginia for New York in August 1776, his troops, especially the Ethiopian Regiment, decimated by disease and defeated in the Battle of Gwynn’s Island, there were 250 people aboard who had been enslaved by some 90 Tidewater families. On those ships were eleven women and four men who had escaped from Willoughby.

When the war ended, many of these Tidewater enslavers, including John Willoughby Jr., traveled to New York City to try to reclaim their human property. But the British refused, unwilling to break their promise of freedom to Black Loyalists. Unable to secure their freedom in America, some 3,000 Black refugees, including 800 formerly enslaved Virginians, emigrated to Nova Scotia under British protection. Among them were seven people who had escaped Willoughby Point on that moonlit night, the only known survivors of the Great Willoughby Slave Escape. 

Learn more about the Willoughby survivors and their eventual journey to Sierra Leone in our new entry.

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One thought on “The Great Willoughby Slave Escape”

  1. Thank you. It was new information for me that whole families, including many children, escaped together in such difficult conditions.

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