Sailing the Chesapeake to freedom

During the late 18th century through the middle of the 19th century, a network of land routes helped enslaved people escape to their freedom. What the history books often leave out, however, is that waterways were a major part of these routes, none more so than the Chesapeake Bay.

The Chesapeake Bay’s overlooked role in American history

While it is certainly true that many people escaped over land, most of those whose journeys took place entirely on foot likely started their path farther north and traveled a much shorter distance in comparison to many of the freedom-seekers from the Deep South.

For those starting their journey in southern states, it was almost impossible to get to the North without having to cross water. Escaping by water aboard a northbound ship or crossing rivers in the middle of the night helped countless people escape to freedom. These networks of maritime routes and ship captains aiding the effort came to be known as the Maritime Underground Railroad.

With the Chesapeake region being the defining point between the southern states and freedom up North, it became a high traffic area for those embarking on their journey to freedom. The geographical landscape of the region often made waterways a necessary part of their routes, with 70% of all published escape narratives mentioning fleeing by water as a means of finding freedom.

Maritime journeys were also some of the faster and safer methods to freedom, with there being fewer places that freedom-seekers could be discovered. While there were still many risks for traveling by water such as mandatory ship inspections, thousands of enslaved people were still willing to make the effort for their freedom.

Seaports and Escape Routes

Virginia waterways offered some of the most critical ports along the Underground Railroad. One of the largest at the time, Norfolk had every type of vessel imaginable, as well as enslaved people that knew how to operate them or were willing to exchange onboard labor for transportation up North.

While Norfolk offered the best opportunities for escape as a major transportation hub during this time, it certainly was not the only one. In Maryland, Baltimore, Annapolis and the Eastern Shore  were other hotbeds of activity. Free Black sailors called blackjacks often hid freedom seekers in the cargo hold of their ships or carried their messages to distant family members. With large plantations located on or near waterways, enslaved people were often knowledgeable about ships and maritime activities. Their expertise in knowing the ways of the water were an advantage for them in planning their escapes. 

Stories Carried by the Water

One of the most well-known stories of using water to escape is that of Harriet Tubman, who relied heavily on the rivers, tidal marshes and coastal routes of the Bay while guiding enslaved people to freedom. Waterways provided not only transportation, but also concealment. The Chesapeake’s network of creeks, wetlands with tall grasses and inlets made it difficult for pursuers to track movement, especially at night.

Water also provided an initial escape route for Frederick Douglass—although his first plan for escaping to freedom was uncovered. Douglass planned to take a log canoe from William Hambleton and sail to the head of the Bay, noting that if they were to take the land route, they would be subject to “interruptions of every kind.”

Born along the Chesapeake, Douglass wrote, “It cannot be that I shall live and die a slave. I will take to the water. This very Bay shall yet bear me into freedom.” Although his initial plan was discovered, he was able to escape a few years later through disguising himself as a free Black sailor and using the knowledge of ship and sailor language that he had learned through growing up in a major port.

Today, the Chesapeake region still holds traces of this history through its historic ports, preserved lands and waterfront towns that stand as reminders that the water was an integral part on the journey to freedom for so many.

(photo credits to Will Parson/Chesapeake Bay Program)