Laying the Foundation in Cape Charles
How does a small town make the case for investing in Main Street? For Cape Charles, Virginia, the journey began with a simple but essential question: What value will this bring us?
This “bonus track” in the Value of Main Street series (Part 1 & Part 2) tells the behind-the-scenes story of how Cape Charles Main Street (CCMS) built early momentum—and lasting value—through grassroots leadership, strategic partnerships, and a clear vision for revitalization. It’s the blueprint between idea and impact.
When CCMS began its journey in 2016, Cape Charles was still finding its footing. With just over 1,100 residents, no town staff dedicated to economic development or marketing, and limited fiscal resources, the idea of investing in a nonprofit Main Street organization required trust, education, and persistence.
“It took a while for the whole council and mayor to see this wasn’t just a special program. It was filling critical economic roles we had no capacity for.”
– Tammy Holloway, former CCSM Board President and current Town Council member
The first steps were grassroots. A committee of local advocates researched the Main Street Approach, then successfully lobbied for the Town’s support and funding by 2017. A town-appointed task force established the first Community Enhancement Board, which evolved into today’s CCMS board. Early board representation from the Town Council, Planning Commission, and Historic District Review Board ensured strong alignment with town priorities.
Key Steps: There are several steps in starting a Main Street organization. The most important step is to increase awareness of the need for downtown revitalization and what a Main Street organization can do to address that need and then form the appropriate organizational structure.
CCMS focused first on structure—securing 501(c)(3) status, becoming a DHCD Commercial District Affiliate (now Exploring Main Street), and introducing the Main Street Approach through community workshops and visioning sessions. With help from Virginia Main Street staff, the organization began to build capacity, form committees, and hire a part-time program manager.
By 2018, the downtown transformation was highly visible. Renovations surged, and 14 new businesses opened. The Cape Charles Business Association merged into CCMS, consolidating leadership and focus. That same year, skeptical Town Council members were invited to tour Gloucester’s successful Main Street program—an eye-opening experience that further strengthened local commitment.
With structure, partnerships, and momentum in place, Cape Charles became the first community to join Virginia Downtowns—a pilot predecessor to today’s Mobilizing Main Street program. Over two years, CCMS deepened its capacity and commitment, ultimately achieving Advancing Virginia Main Street designation in fall 2020.
What made the difference?
Community engagement. Stakeholder buy-in. Visible, incremental wins.
“We showed what was possible, and built trust step by step.”
– Tammy Holloway, former CCSM Board President and current Town Council member
Virginia Main Street 