Chesapeake Bay Maritime Museum (CBMM) can always be counted on to provide groundbreaking programs. Once again, they do not disappoint. Their latest exhibit, Sailing to Freedom: Maritime Dimensions of the Underground Railroad, opened on September 27, 2024, and offers visitors a fresh perspective on one of the most critical and compelling periods in American history: The Underground Railroad. But this time, the focus is on a lesser-known part of that story—escape routes to freedom by sea.
Through immersive storytelling, compelling artifacts, and deep historical research, the CBMM)dives into the maritime aspects of the Underground Railroad, shedding light on the lesser-explored routes enslaved African Americans took to liberate themselves via coastal waters. From the log canoes of the Chesapeake Bay to the large ships on the Atlantic, the exhibition explores the ways freedom seekers navigated the waterways, sometimes risking everything for a chance at liberty. It is designed as a self-guided tour, allowing visitors to explore the compelling stories at their own pace
Curated by the New Bedford Whaling Museum’s Maritime History Curator Michael Dyer and Professor Timothy Walker of the University of Massachusetts-Dartmouth, Sailing to Freedom takes inspiration from the book of the same name, which featured essays from over ten scholars, two of which heavily feature the Chesapeake. For CBMM, it was a natural fit. Jen Dolde, CBMM’s Director of Curatorial Affairs and Exhibitions, explained, “We knew that Chesapeake played a central role in this, and we knew that we wanted to enhance this story, both the story that’s already told with objects from our collection, but also saw opportunities to make it our own.”
While the original exhibition focused on broad aspects of the maritime Underground Railroad, CBMM added a local dimension, including key figures of the Chesapeake. The exhibition invites visitors to reconsider the long-held assumption that the Underground Railroad traveled by Harriet Tubman was strictly a land-based network. Instead, it highlights the crucial role waterways like the Chesapeake Bay played in the freedom-seeking journeys of enslaved people. Dolde noted, “People assumed that Tubman always used land routes, but we know that water played a huge part in her life, both in her work as an enslaved person and as she helped others to seek freedom.”
Also receiving attention is Frederick Douglass’s story, particularly his early experiences as a caulker in the shipbuilding industry. His knowledge of the maritime world and connection to the water played a critical role in his path to freedom. Said Jill Ferris, CBMM’s Vice President of Education & Interpretation, “Douglass was from here, and he knew the comings and goings of ships. His understanding of the maritime world helped him when it came time for his own escape.”
The exhibit also examines how escaping via the sea was not a simple attempt and came with immense risk. Many enslaved people were able to find freedom because of their knowledge of the sea or through their labor in maritime industries. For others, secrecy and daring were the only strategies available.
Said Dolde, “A lot of people may not be aware of the role water played in these stories. Some freedom seekers forged or borrowed protection papers that allowed them to board ships; others simply had access to waterways because of their work. This exhibition humanizes those stories, putting names to individuals and showing the risks they took.”
One of the many strengths of Sailing to Freedom lies in how CBMM incorporates objects from its collection to bring history to life. Visitors will encounter powerful artifacts that speak to both the struggles of enslavement and the triumph of self-emancipation.
Among the artifacts on display is a log canoe model representing the types of small boats used by freedom seekers in the mid-1800s. These vessels, though modest in size, were critical in allowing enslaved people to navigate through the treacherous waters of the Chesapeake Bay, sometimes with their families in tow. Ferris also pointed out that the museum includes “tools used by enslaved people working in the shipbuilding trade, which remind us how intimately African Americans were tied to the maritime industries.”
A portrait of the Katherine Jackson, a ship used to transport 272 enslaved African Americans from Maryland and Washington, D.C., to sugar plantations in Louisiana, serves as a sobering reminder of the brutal legacy of the domestic slave trade and the specific history of the Chesapeake region. “This portrait shows the darker side of the story—the forced sale and transport of enslaved,” said Dolde.
The exhibit also features a profoundly poignant quilt loaned by the Universal Sailing Club, commemorating the 10th anniversary of the Souls at Sea celebration ceremony. Crafted by National African American Quilt Guild members, the quilt depicts 14 ships involved in the transatlantic slave trade, offering a visual representation of the many vessels that carried captive Africans to the Americas. It’s a stunning, reflective piece that connects past atrocities to modern-day efforts to remember and heal.
Perhaps one of the most captivating figures visitors will meet in the exhibition is Henry “Box” Brown. Brown famously escaped from slavery in 1849 by shipping himself from Virginia to abolitionists in Philadelphia in a wooden crate. His story of endurance and creativity is almost hard to believe, and CBMM has found a powerful way to bring this incredible tale to life.
As part of its Museum Masters summer camp, CBMM invited middle school students to research Brown’s story, examine historical manuscripts, and recreate the box he used to ship himself to freedom. The crate, constructed to scale by these students, now sits in the exhibition, providing an intimate and tangible connection to Brown’s ordeal. Ferris described the impact of having students engage in this hands-on historical project: “They looked at the primary sources, looked at the documents, took the measurements, and constructed to size. It’s an incredible way to make history real and accessible.”
Brown’s escape took 27 grueling hours. He faced extreme physical discomfort inside the cramped, dark crate, but his determination to reach freedom was greater than the risk. Ferris said, “It’s a story that’s easy to connect with because you can imagine yourself in his shoes, the fear, the desperation, and the hope–to think, from his perspective, what it would be like to literally mail yourself to freedom.”
One of the most exciting aspects of Sailing to Freedom is the interactive story map, which allows visitors to explore the history in greater depth. As Dolde explained, “We’ve incorporated a story map (accessed via a QR code) that we anticipate and want to grow during the course of this exhibition. It’s a way for people to explore more stories geographically, and we’ll continue adding to it.”
CBMM also encourages visitors to explore related sites throughout the Chesapeake region. The exhibition includes brochures and maps to direct people to other locations linked to the Underground Railroad, allowing them to extend their learning beyond the museum.
Sailing to Freedom is a must-see for those interested in untold stories, courageous journeys, and a fresh perspective on the Underground Railroad.
The exhibit will run throughout 2025, and entry is included with CBMM’s general admission. As with all CBMM programs, members receive free access.
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