For the last two years, Woodberry Forest School senior Jayden Crosby-Brewer has researched the lives of the enslaved people who lived on and cared for the land prior to the school’s founding, when the site, north of Orange in Madison County, served as the home of William T. Madison, brother of former President James Madison.
On Saturday, May 16, community members will have an opportunity to celebrate the results of that research. During a commemoration ceremony at 2 p.m., Woodberry Forest School will recognize 53 individuals, enslaved by William Madison, whose labor and legacies are inextricable from the history of the school, and from the larger history of Madison County.
Crosby-Brewer said that his interest in researching this topic was initially sparked by a comment at a Woodberry Forest graduation ceremony.
“I found out there was a plantation through our headmaster, who mentioned at graduation that this land was founded by enslaved people,” he said.
That led him to explore more, from meeting with former Black employees and alumni of the school, to engaging with historians at Montpelier; Right the Record, an initiative that uncovers and documents the history of Black, indigenous and other marginalized people in Virginia; the Orange County African-American Historical Society and more.
Crosby-Brewer said that one particular document provided by Montpelier helped to solidify the vision for his project — to recognize each of the enslaved persons not only for their labor, but as individuals. That document, an 1843 “property inventory” by William Madison, listed the names of 53 people who were enslaved by the Madison family.
The limited information included in the inventory means that there is still plenty to be discovered — when they lived and died, who they loved and what type of work they did — but there are glimpses. An enslaved woman named Lauretta had a son named Albert. Two of the individuals listed, Simon and Betty, were a married couple.
Another piece of information that Madison did think to include — their prices — provides additional clues. Henry, who was listed at $25, a price far lower than the healthy adult males on the inventory, was likely elderly and unable to do more than light work, Crosby-Brewer said. Peter, listed at $75, was likely a child.
During Saturday’s event, attendees will have an opportunity to hear each of the 53 names of these individuals, and to see a “sneak peek” of a commemorative bench inscribed with them.
Take action
Learn about 53 enslaved persons who were integral to the history of Madison County
Woodberry Forest School and senior Jayden Crosby-Brewer will host a commemoration ceremony on Saturday, May 16, honoring the enslaved individuals whose work contributed to the site that would ultimately become the school.
The event will take place at 2 p.m. in the memorial garden outside of The Residence, the former home of William T. Madison which was built by enslaved laborers, located at 898 Woodberry Forest Road in Madison. Attendance is free but registration is required. To RSVP, email Mandy Alexander, Director of Strategic Communications, at mandy_alexander[at]woodberry[dot]org or call 540-672-6717.
The ceremony will take place at the new memorial garden just outside of The Residence, Madison’s former home, which was built by the people he enslaved and now serves as a lodging and event site for the school.
“Woodberry is such a widely known school, and my hope is that we’re able to give those who worked and were enslaved here, and were not recognized, that recognition that they have been essentially deprived of for centuries now,” Crosby-Brewer said. “And I think that this is a step in the right direction for the school to start looking more into their past.”
Dr. Mesha Jones, president of the Madison County African-American Historical Society, agrees. Jones said research projects like Crosby-Brewer’s are critical to building a more complete history of enslaved persons, who were not allowed to keep their own written records, and whose lives were often reduced to the most basic details in the property records of slaveowners.
“Projects like this help restore something that history has often denied these individuals — their humanity,” she told Charlottesville Tomorrow. “These 53 individuals that Jayden is going to recognize were mothers and fathers and children that provided so much to the Madison community. So, the power in speaking their names and researching their lives, it’s allowing them to remain visible.”
As someone whose own organization works to document and preserve the history of Black communities in Madison County, Jones said she’s encouraged to see Woodberry Forest students and faculty adding to the knowledge base.
“There is a group of educators at Woodberry that I’ve found in the last year or two, who are really pouring into the students and allowing them the space and time to do this research, so I commend them for this,” she said. “The work reflects a willingness to really engage honestly with the past, while helping them continue to grow and ask questions, and also educate those in the community of Madison.”
Editor’s note: This article was updated on May 13, 2026, to correct the RSVP information for the commemoration ceremony.
