Welcome to Winchester Main Street

Old Town Winchester, one of Virginia’s oldest Main Street programs, was designated in 1985. Historically, the program has been administered by the municipality—first by the City of Winchester and more recently by the Economic Development Authority (EDA).

In fall of 2022, Winchester received a visit from Main Street America (MSA) as part of a Transformation Strategy service funded by Virginia Main Street (VMS). MSA recommended that Winchester explore the possibility of restructuring to further their local initiative and improve its long-term sustainability. The (then) Main Street steering committee began conducting informational interviews with fellow Advancing Virginia Main Street (AVMS) organizations. What they learned was that most local Main Street initiatives—in fact, all in Virginia (per VMS Program Guidelines)—were administered by an independent, nonprofit organization that works in partnership with the municipality.

Winchester Main Street (WMS) spent the remainder of 2023 developing their foundational documents and working with an attorney to file all the necessary paperwork to officially form. The new board of directors created new mission and vision statements, bylaws, and a policy and procedure handbook. In early 2024, city council approved a resolution dedicating municipal financial support.

With operational funds secured, WMS looks forward to hiring their first full-time executive director this spring. And, thanks to a VMS Downtown Investment Grant (DIG), they will soon begin work with consultants to develop branding for the organization, along with funding and strategic plans. Restructuring also allows them the ability to expand community support and buy-in by establishing volunteer committees and soliciting donations and sponsorships—not to mention, it opens the door to many new grant opportunities.

To keep the community up to date throughout the transition, WMS is hosting monthly outreach and input sessions. VMS is proud of Winchester’s organizational transformation and commends the community’s determination as they work to standup a new organization, all the while maintaining their regular, annual programming!