History of Black Labor
Below is a look at how Black labor at Woodberry Forest has evolved over the years. From the enslaved individuals who worked this land before the school existed, to the generations of Black workers who built their lives here after emancipation, to the staff members who walk these grounds today, this history spans more than 200 years. It is a story of dignity, resilience, and an enduring connection to a place that has meant many things to many people across many generations.
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1794–1843
The Foundation
In 1794, James Madison Sr. gave his son William Taylor Madison 1,300 acres in Madison County, Virginia. William named the plantation Woodberry Forest. The Residence, believed to have been designed by Thomas Jefferson, was built in 1793 and became the heart of the plantation. It was home to William and his family, and it was maintained entirely by the people he enslaved.
By the time William Madison died in 1843, 53 souls, 31 adults and 22 children, were documented in the 1843 Inventory of The Residence. They had names. They farmed a working dairy plantation, cooked the meals, maintained the grounds, and kept the household running. Their labor was total. Their freedom was not their own.
After William's death, he divided the 1,300 acres among his living children and grandchildren. His son Ambrose Madison inherited over 400 acres, including The Residence. Ambrose died in 1855, and his widow continued to live there until around 1862. By then, the Civil War had reached Virginia, and the world that had sustained Woodberry Forest as a plantation was coming apart.
The impact of this history reached far beyond the plantation's gates. By 1860, 60% of Orange County's population was Black, the backbone of an entire region built on their labor. Descendants of those enslaved at places such as Woodberry and Montpelier still live in the surrounding communities today, in places like Tanner's, whose residents have been connected to this land across generations.
1865–1889
The Transition
When the Civil War ended, the legal terms of labor changed, but the land, the work, and the people often stayed the same. In 1870, John S. Walker purchased the land for his son, Robert Stringfellow Walker, who would go on to establish Woodberry Forest School in 1889. The Residence, which had stood since 1793, remained standing through all of it, through slavery, through war, through transition, and it stands today.
During those years between emancipation and the school's founding, formerly enslaved individuals gathered in nearby settlements, communities like Tanner's and the Forest along Arrowpoint Road, and many came back to Woodberry looking for paid work on the same grounds where they had been enslaved. Frank Walker, a descendant of the founding Walker family who grew up working this land alongside descendants of the formerly enslaved, described the transition simply: 'People who have been slaves are now coming back to work on the same place to be paid... got hired to do the same job, but this time they were being paid for it.'
The work itself, cooking, groundskeeping, farming, and housekeeping, was carried out almost entirely by Black workers. Their labor fed the school, maintained its buildings, and kept its daily life running. Beyond wages, workers received housing, food, and shared resources, an arrangement that provided some stability even within an unequal system. And the workers who came were not uneducated or unskilled. Black schools in Orange County grew quickly after the Civil War because the community understood that education was a matter of survival. Every Black worker who came to Woodberry during this era could read, something the historical record has largely overlooked.
Outside of Woodberry's gates, Black churches became the anchors of these communities, providing stability and a sense of home across generations. Workers who spent their days in Woodberry's kitchens and fields came home to congregations that had existed since before the Civil War, some celebrating over 180 years of continuous service to this day. They were trusted, skilled, and essential. And yet the structure of the era kept things unequal. Respect existed, but within limits, a tension that would define Black labor at Woodberry for decades to come.
1889–1970s
The Earlier Years
By the mid-20th century, Black families weren't just working at Woodberry. They were living there, raising children there, building entire lives within its borders. Woodberry wasn't just a school. It was a self-sustaining community that ran its own dairy, its own farm with cows and hogs, its own laundry where staff washed every bedsheet and tablecloth on campus. Most of that work was done by Black workers, and they were deliberately kept in their place.
The rules were not subtle. Black workers used back doors, not front doors. They ate in a separate dining room downstairs. Some workers who lived on campus were housed in fenced cabins on the ridge above the outdoor pool and were not allowed to move freely beyond those fences without permission. As one man whose uncle lived in those cabins recalled, when his father visited, and they wandered outside the fence, the business manager tracked them down, removed his father from campus, and told his uncle to get back inside if he wanted to keep his job. His uncle left not long after. Black workers were essential to Woodberry's survival. Their movement was not their own.
The work ethic these workers brought despite all of that was something else entirely. They walked through the snow to get to work. They rarely missed a day. They took pride in what they did, even when the institution didn't fully acknowledge who they were. As one daughter of a Woodberry groundskeeper said of her father: 'Anything he did, he took pride as if it was his own, even though he knew it wasn't his own.' That wasn't blindness to the situation. That was a choice: to hold on to dignity in a place that wasn't always willing to give it.
Still, the relationships that formed within those constraints were real. There were faculty members who broke unwritten rules and personally made space where the institution hadn't. Those moments stood out because they were rare, but they also showed that what existed between Black workers and the Woodberry community was never purely about labor. It was human, and at times genuinely kind in ways the outside world, still deep in segregation, rarely was.
Beyond campus, Woodberry played a real role in the broader Black community of Orange County. When public facilities were closed to Black residents, Woodberry opened its gymnasium for community basketball, supported Black youth organizations, and trained young Black residents in skills they couldn't access anywhere else. As one community member whose family has been connected to this land for six generations put it: 'Woodberry was a lifeline to a lot of these people.' The school was never going to make anyone wealthy, but it gave people stability and opportunity when both were hard to find. That went both ways. The community gave Woodberry generations of loyal, skilled workers, and Woodberry gave the community something to hold onto.
1970s–2000s
Breaking New Ground
As the decades passed, things at Woodberry started to slowly shift, though slowly is the right word. For most of the school's history, Black workers had been kept in the same roles: the kitchen, the dining hall, the grounds, the farm, and housekeeping. The hierarchy was clear and deliberately maintained. Black workers were essential to the institution's daily life, but leadership remained out of reach. As one person who spent decades at Woodberry and witnessed this firsthand observed: 'There were never people in leadership. Even though certain departments were predominantly Black, there was never a Black person in leadership. There were always whites in leadership of various departments.'
The reality of this era was hard. Racist slurs were written on bathroom walls, and Black housekeeping staff quietly washed them off so Black students wouldn't have to see them. Black male workers were told by those who came before them not to look white women in the eyes when passing in the hallway, a rule passed down as a matter of survival. A longtime food service worker shared what an earlier worker had told him: 'If they walk down the hallway and see a white woman walking down the hallway at the same time, the men couldn't look at the white woman. They had to turn their head or look down while passing by.' These weren't old stories from a history book. They were living memories carried by people who still walked these halls.
Change came slowly, and often through small moments that meant more than they should have. For years, Black workers weren't invited to the school's main Christmas party, held upstairs with food and a band, while white staff celebrated above them. When a headmaster finally opened that event to everyone, it meant something real. As one Black worker reflected: 'Opening up that big event to everybody was, I think, a significant gesture. We don't just value you because of your work. We value you.' That some white staff stopped attending once Black workers were included says everything about how fragile that progress was.
Within the kitchen, the dining hall, and the hallways of this school, Black workers had been building something powerful all along, not through titles, but through presence. A housekeeping staff member who stood in the hallways and greeted students by name every single day became a fixture of campus life, someone students looked forward to seeing, someone who made Woodberry feel like a place that knew them. Dining hall workers who quietly recognized students, remembered faces, and made people feel seen created a warmth that no official program could manufacture. Workers in food service became so woven into the fabric of student life that students and alumni recognized and openly celebrated them. That kind of relationship, built over years of showing up, is its own form of leadership.
By the late 1990s and into the 2000s, Black staff members began moving into administrative and leadership roles for the first time. Black administrators began shaping admissions, student life, and the school's direction in ways that had never been possible before. One administrator used their position to deliberately bring more Black students to campus, knowing that when Black students arrived and excelled academically and athletically, it changed what was possible for everyone who came after. Others created unofficial but deeply necessary spaces where students of color could process their experiences on a predominantly white campus, track grades, absorb hard moments, and make sure students had somewhere to land. That kind of care was never in any job description. It was given freely. As one Black staff member who did this work described it: 'I want to be remembered as somebody who cared enough to do something about that and create a home away from home for the boys.'
And through it all, the long tradition of Black labor in the dining hall and kitchen continued, carried by workers who had given decades of service and represented a direct connection to an earlier era. One by one, the people they had worked beside retired, moved on, or passed away, until those who remained were the last ones left who remembered how it used to be. As one dining hall worker who gave over 40 years to Woodberry put it: 'I'm the last of the African American ones for the kitchen at this time frame.' That is not just a personal reflection. That is a historical marker, the end of one chapter and the beginning of another.
2000s–Today
The Present
Today, Black labor at Woodberry looks different than it ever has. Black staff members have moved into leadership roles across the school, in admissions, administration, coaching, and faculty positions that shape student life every single day. Black professionals now sit on the Board of Trustees, bringing the voices and perspectives of a community that built this place into the room where decisions are made. The presence of Black professionals across more parts of campus than ever before reflects a change that workers from earlier generations could not have imagined, and that they made possible through decades of showing up.
But the through line is still there. No matter the role, dining hall, housekeeping, coaching, administration, or the boardroom, the Black men and women who have worked at Woodberry describe the same thing. The work was never just the work. It was the relationships. It was showing up every day and making sure students knew someone saw them. It was mentorship that went way beyond any job title. As one current staff member put it: 'Woodberry shaped me mentally, physically, professionally, at home. Just overall as a man.'
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Our understanding of this legacy is always evolving as we uncover new details. If you have any insights, memories, or corrections that could change or deepen this research, please share them below to help us grow.
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