The Jefferson School & United Way: A Legacy of Impact on Greater Charlottesville’s Stories

Could you please tell us a little bit about yourself and your relationship to Jefferson School and Jefferson School Foundation?

My name is Kimberly Sheffield, and I serve as the Executive Director of Jefferson School Foundation. Before stepping into this role, I served as the Foundation’s Director of Community Engagement, so much of my work has centered around building relationships, creating meaningful partnerships, and helping our community feel connected to Jefferson School.

For me, this is more than a job. Every day when I walk through these doors, I feel the history, love, and responsibility that come with this building. Sitting in my office and thinking about the great minds and community leaders who once occupied these same spaces is incredibly humbling. Jefferson School has become a part of who I am and I feel deeply honored to help care for its legacy.

To you, what role does Jefferson School play in our community?

Jefferson School is a place of history, but it is also a place of life, movement, and possibility. It has always been a place where people gathered, learned, built relationships, and found community. Today, it continues to serve as a home for nonprofit organizations, businesses, artists, educators, health and wellness programs, cultural organizations, and community events. It is a place where the past and the present meet. Jefferson School reminds us of where we have been, but it also challenges us to think about where we are going. It belongs to the community, and our responsibility is to make sure people continue to see themselves reflected in this space.

Jefferson School Foundation helps UWGC share meaningful stories with our community through your support of Envision Radio. Why was this a program Jefferson School Foundation decided it wanted to support?

We decided to support Envision Radio because it gives people the opportunity to tell their stories in their own voices. Oftentimes, we are working in silos, and many of us may believe that we have nothing in common with one another. But when you take the time to listen to these stories, you begin to hear the common threads that connect us. Every story may look different, but so many of them are rooted in grit and resilience, qualities that we all carry.

How do you feel storytelling helps build and foster community?

Storytelling allows us to see ourselves in one another, better understand the work happening around us, and recognize that we are often more connected than we realize. It reminds us that behind every organization, program, movement, or historic moment, there are real people and real experiences. Stories allow elders to pass down memories, help younger people understand the sacrifices that came before them, and give people who may feel unseen an opportunity to be heard. It creates empathy, strengthens relationships, and gives people a reason to care about one another and the community around them.

What has been one of the most impactful stories you have been a part of or witnessed in your experiences at Jefferson School?

One of the most impactful experiences has been hearing from Jefferson School alumni and descendants about what this building meant to them and their families. When people walk into the building and begin pointing to the places where they attended class, where a parent or grandparent taught, or where a family member worked, you can immediately see that Jefferson School is not simply a building to them. It is personal. It is a part of their family’s story. Those moments remind me why preserving this space matters. We are preserving memories, sacrifices, relationships, and the stories of generations of people who helped shape this community.

Jefferson School is celebrating its 100th anniversary this year. Could you share more about the school’s century-long history?

The 1926 portion of Jefferson School turns 100 years old this year. For generations, Jefferson School served as an important educational and cultural institution for Charlottesville’s African American community during a time when segregation limited where Black children could learn and what opportunities were available to them. The school was a place where educators poured knowledge, discipline, pride, and love into their students. Teachers often knew not only the children they taught but also their parents, siblings, and extended families. It was a true community school.

Over the years, the building has continued to evolve, but its importance has never disappeared. Today, Jefferson School City Center is home to organizations and programs that serve thousands of people through education, history, recreation, health, entrepreneurship, literacy, culture, and the arts. Reaching 100 years gives us an opportunity to honor the people who walked these halls before us while also recognizing the new history being created here every day.

Are there any events or opportunities you have planned for this year to celebrate 100 years?

Yes! We are incredibly excited to celebrate this milestone with Two Events, One Celebration on August 10, 2026. We will begin with a special alumni and descendants reception. This will be an intimate opportunity for former students, descendants, and friends of Jefferson School to reconnect, share memories, enjoy music and food, and reflect on the journey of Jefferson School.

Later that evening, we will move outside for 100 Years Strong: A Legacy Run, in partnership with Prolyfyck Run Creww and Soul of Cville. The community celebration will include music, food, art, fellowship, a special performance, and a symbolic passing of the torch from one generation to the next. People do not have to participate in the run to attend. They can walk, cheer, enjoy the celebration, or simply be present. We want the entire community to feel welcome because this milestone belongs to all of us.

Jefferson School’s impact in its first 100 years has left an undeniable mark on our community. What do you hope for its next century?

For the next 100 years, I hope Jefferson School continues to be a place that is deeply rooted in the community, a place where people feel welcomed, valued, connected, and inspired. I hope the younger generation understands the importance of this place, loves this place, and feels a responsibility to activate it. I want them to understand that Jefferson School is not simply a historic building. It is a living part of our community, and they have a role in determining what happens here next.

I want Jefferson School to continue being a place where community organizations grow, entrepreneurs are supported, young people discover new possibilities, artists create, families gather, and important conversations happen. Most importantly, I hope we never lose sight of the people whose courage, hard work, and love made Jefferson School what it is. Our responsibility is to honor their legacy while continuing to create opportunities for the next generation to build their own relationship with this place.

The first 100 years created an incredible foundation. My hope is that the next century will be just as powerful, just as impactful, and filled with even more stories of community, opportunity, legacy, and love.