ST. MICHAELS — Frederick Douglass, the ardent abolitionist and social reformer, was born into slavery on the banks of Tuckahoe Creek in Talbot County and later became its most famous son.

Like the county’s shoreline, fractured by waterways and necks, the Talbot’s history is divided, too — torn between producing the 19th century’s foremost leader of African American civil rights and upholding the very institution that enslaved him.

Next week, the Chesapeake Bay Maritime Museum will explore that contrasting heritage in its newest exhibit, “Bear Me Into Freedom: The Talbot County of Frederick Douglass.”

“People are still wrestling with the legacy of slavery, and I think that’s true in Talbot County, too,” said Jenifer Grindle Dolde, the museum’s director of curatorial affairs and exhibitions. “Douglass lived here, but what does that really mean?”

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The exhibit focuses on Douglass’ first 20 years as a young man enslaved by Aaron Anthony, an overseer on the Wye House plantation, and later by Anthony’s son-in-law, Thomas Auld, who “rented out” Douglass to Eastern Shore farmers and sent him to relatives across the bay in Fells Point.

Eventually, Douglass broke free of his chains — both literal and metaphorical — and escaped slavery as a 20-year-old before becoming a well-established author, orator and human rights advocate.

“Douglass was not defined by his enslavement, but that’s what his life in Talbot County was and it’s important to remember that,” Grindle Dolde said.

“At the same time,” she added, “we’re not the place we were 150 years ago.”

Silhouettes of slavery

In Douglass’ first memoir, published in 1845, he writes: “Why am I a slave?”

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His question greets guests as they enter the exhibit and reverberates throughout it.

During a tour, Grindle Dolde and Jim Koerner, the museum’s exhibition designer, explain how the exhibit excerpts from Douglass’ autobiographies that describe how he experienced slavery.

Thursday, Feb. 19, 2026 — The Chesapeake Bay Maritime Museum is opening a special exhibit titled "Bear Me Into Freedom: The Talbot County of Frederick Douglass," which explores Douglass' life in Talbot County, where he was born enslaved.
The exhibit focuses on Douglass’ first 20 years. (Jerry Jackson/The Banner)
Thursday, Feb. 19, 2026 — Jen Dolde, director of curatorial affairs & exhibitions at The Chesapeake Bay Maritime Museum, gives a preview tour of exhibit "Bear Me Into Freedom: The Talbot County of Frederick Douglass,"
Jenifer Grindle Dolde, director of curatorial affairs and exhibitions at the Chesapeake Bay Maritime Museum, gives a preview tour of the exhibit. (Jerry Jackson/The Banner)

“Everything is guided by his words, and we’re just augmenting that,” Koerner said.

Key among those augmentations is an interactive hologram in which visitors can ask (a pixelated version of) Douglass about his life.

Grindle Dolde explained that guests will receive responses from an authentic representation of Douglass’ voice created by a closed-loop AI built with primary and secondary source materials written by or about Douglass.

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Koerner also said he decided to superimpose silhouette figures onto images of Talbot County by local photographer Jeff McGuiness, who published a photo book featuring buildings and scenes prominent in Douglass’ life there, to create a human connection to the exhibit’s narrative.

One excerpt — highlighted from “My Bondage and My Freedom,” Douglass’ second autobiography — recalls how he slept inside a closet on the Wye plantation and used a burlap sack as a blanket.

An AI version of Frederick Douglass will answer questions about his life as part of the exhibit. (Jerry Jackson/The Banner)

Koerner built a door and placed it next to an enlarged copy of the photo McGinnis made of Wye House.

It opens into a closet with the silhouette of 6-year-old Douglass kneeling inside. Above the boy, Douglass’ quote reads:

“I slept, generally, in a little closet, without even a blanket to cover me. In very cold weather. I sometimes got down the bag in which cornmeal was usually carried to the mill, and crawled into that. Sleeping there, with my head in and feet out, I was partly protected, though not comfortable.”

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“The question was how do we communicate this and make it interesting for people to walk through?” Koerner said. “The silhouettes allowed us to show Douglass without showing Douglass.”

Thursday, Feb. 19, 2026 — As a young enslaved child in Maryland, Frederick Douglass slept on the floor of a small, cold, and crowded closet. The Chesapeake Bay Maritime Museum’s special exhibit titled "Bear Me Into Freedom: The Talbot County of Frederick Douglass," features depictions of Douglass’ life in Maryland.
As an enslaved child, Douglass slept on the floor of a small, cold and crowded closet. (Jerry Jackson/The Banner)

Reclaiming Douglass’ humanity

In 1833, after Auld inherited Douglass through his first marriage, he sent him to Edward Covey — an Eastern Shore farmer known as a “slave breaker.”

Auld wanted to crush Douglass’ rebellious spirit after subjecting the 16-year-old to a year of starvation on his property.

The man who went on to become the leader of the country’s abolitionist movement and an informal adviser to President Abraham Lincoln was broken initially by Auld’s cruelty.

Douglass recalled his enslaver as a man who took pleasure in making him “feel the painful gnawings of hunger.”

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Nearly 200 years later, Auld’s grave — slightly overgrown and unremarkable — sits a little over half a mile from the maritime museum in St. Michaels.

Tarence Bailey Sr. (right), Frederick Douglass' great-great-great-great-great grandnephew, poses with his son, Garry Perry, and wife, Michelle Banks-Bailey, during a celebration of Douglass' birthday on Saturday, Feb. 14, 2026 hosted by Tarence Bailey Sr.'s non-profit The Bailey-Groce Family Foundation, Inc.
Tarence Bailey Sr., right, Frederick Douglass’ great-great-great-great-great grandnephew, with his son, Garry Perry, and wife, Michelle Banks-Bailey, during a celebration of Douglass’ birthday on Feb. 14. (Courtesy of Tarence Bailey Sr.)

The irony that an exhibit honoring Douglass is a 10-minute walk from his enslaver’s final resting place does not escape Douglass’ great-great-great-great-great grandnephew, Tarence Bailey Sr.

“I keep a picture of Thomas Auld’s tombstone in my phone,” he said. “So, whenever I’m starting to doubt that I can get anything done or I’m starting to feel down, I look at that tombstone and it gives me energy because I’m like, this guy would love to see me down and feel like I need to quit.”

A descendant’s perspective

Bailey is a direct descendant of Betsey Bailey, Douglass’ grandmother, and Modesty Green, Harriet Tubman’s grandmother.

Tubman also was born into slavery on the Eastern Shore, about 40 miles south of Douglass near the Blackwater National Wildlife Refuge in Dorchester County.

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Bailey has dedicated the past 20-plus years to raising awareness of his ancestors’ ties to the region, which he said has rarely acknowledged its role in slavery.

“When I was growing up in school, they didn’t teach Black history as if it happened here,” he said. “They talked about Harriet Tubman and Frederick Douglass extremely briefly. You might have got maybe 10 minutes for each.”

The area’s ignorance, coupled with Bailey’s discovery of his ancestry later in life, led him to establish a nonprofit called FD on the Hill — a reference to Easton’s historic Black community — to preserve Douglass’ legacy and Talbot County’s rich African American heritage.

The Chesapeake Bay Maritime Museum in St. Michaels. (Jerry Jackson/The Banner)

The 50-year-old said he supports the maritime museum’s work to honor Douglass in the same town that once enslaved him.

“That particular [exhibit] needs to be in St. Michaels,” Bailey said. “I mean, shoot, I hope it’s big and glorious. You know what I mean? ’Cause it needs to be.”

The exhibit opens Thursday.