A Stronger Downtown Starts with a Stronger Organization: Historic Downtown Tappahannock
Cupper Dickinson and Jovita Kelly have used Mission Elevation as an opportunity to build a legacy for Historic Downtown Tappahannock.
Historic Downtown Tappahannock is helping one of Virginia’s most historic downtowns imagine what comes next.
Set along the Rappahannock River, Tappahannock’s downtown district holds deep history, local character, and significant opportunity. With 14 buildings dating back to the 18th century and a place on the National Register of Historic Places, the downtown reflects generations of community life, commerce, and connection.
Today, Historic Downtown Tappahannock (HDT) is working to build on that legacy. Through preservation-based economic development, support for local businesses, tourism efforts, cultural programming, and community partnerships, HDT is helping bring new energy into the heart of town.
For many residents and visitors, that work is most visible through farmers markets, festivals, parades, and other events that draw people downtown. But for HDT, events are only one part of a larger strategy.
“Our focus, our main purpose, is revitalization in downtown Tappahannock,” shared Cupper Dickinson, Executive Director of HDT. “A lot of people think of us a place that just does events, but we do events to bring people into the downtown.”
That distinction matters. In a small, diverse riverfront community like Tappahannock, downtown revitalization means creating reasons for people to gather, shop, visit, and invest. It means supporting business owners, strengthening tourism, and helping ensure the downtown remains a vibrant center of community life.
It also means responding to real challenges. Over time, Tappahannock has lost businesses that once served as everyday gathering places, including a bakery and a movie theater. Four years ago, those challenges were compounded by a catastrophic fire that destroyed a significant portion of downtown. In the years since, HDT has played an important role in helping the community continue moving forward.
When Cupper and Board President Jovita Kelly joined VCDC’s Mission Elevation program, HDT was navigating both leadership transition and long-term recovery. A Main Street representative encouraged them to apply, seeing an opportunity for HDT to gain “more tools in our tool belt” as the organization looked toward the future.
Their team looked a little different from many others in the cohort. Instead of two paid staff members, HDT participated through a partnership between its executive director and a volunteer board chair. That structure reflected the reality of the organization’s work: ambitious goals, limited capacity, and a strong reliance on board leadership and volunteer support.
Through Mission Elevation, Cupper and Jovita began focusing on the internal foundation needed to sustain HDT’s external impact. Their goals centered on three priorities: raising $100,000 in sustainable funding, building a stronger working board, and growing the volunteer base needed to support long-term revitalization.
Each of those priorities connects directly to HDT’s broader vision for downtown Tappahannock. Sustainable funding would give the organization more stability. A stronger board would expand leadership capacity. A larger volunteer base would make it possible to support more programming, partnerships, and community engagement over time.
Mission Elevation helped HDT move those ideas from aspiration to action. Through the program’s performance challenge process, Cupper and Jovita were able to examine what needed to change inside the organization in order to strengthen its work in the community.
The tools offered through the program helped them break down large goals, identify barriers, and clarify next steps. The program’s emphasis on data also created immediate benefits. When HDT developed its annual report, the information was easier to gather because the organization had already been practicing how to track, collect, and use data more intentionally.
Just as important, Mission Elevation helped Cupper and Jovita strengthen the way they talk about HDT’s work. As HDT continues building support for downtown revitalization, storytelling has become an essential tool — helping community members, partners, funders, and volunteers understand not only what the organization does, but why it matters.
Executive coaching added another layer of support. Through coaching, Cupper and Jovita had space to talk through obstacles, test ideas, and move from planning toward action with greater confidence.
The cohort experience also became a meaningful part of the journey. By connecting with leaders from other organizations, HDT found peers who understood the pressures of capacity, funding, board development, volunteer engagement, and community need. Those relationships offered encouragement, practical ideas, and a reminder that even when the work feels difficult, HDT is not doing it alone.
“It might be in a different industry, but they're definitely facing similar struggles, and they're able to give ideas and insights into things that we might not have thought about,” Jovita noted.
One of the most memorable moments came when the Mission Elevation cohort visited Tappahannock for an in-person retreat. During an art activity, each participant began a picture, passed it along, and watched as others added new layers until the final image looked entirely different from where it began.
The exercise offered a fitting reflection of community work. Revitalization is not created by one person, one organization, or one event. It takes many hands, many perspectives, and a shared willingness to build something together. The visit also gave HDT the chance to see Tappahannock through fresh eyes, as cohort members shared what they noticed and appreciated about the town.
For Cupper and Jovita, Mission Elevation has been both practical and affirming. It has provided tools, structure, coaching, and peer connection, while also reinforcing the value of the work HDT is already doing.
“We both have learned a lot and grown,” Cupper said. “The time is worth it.”
As HDT continues strengthening its board, growing its volunteer base, improving its use of data, sharpening its storytelling, and pursuing sustainable funding, the organization is building the capacity it needs for the long haul.
For Historic Downtown Tappahannock, that capacity is not an abstract goal. It is what makes continued revitalization possible. It is what helps local businesses, residents, visitors, and partners see downtown as a place worth investing in. And it is what will help Tappahannock continue building a downtown that honors its history while creating new possibilities for the future.
