The Main Street America program in Winchester began in 1985 to promote the economic vitality and sustainability of Old Town, focusing on the Primary and Secondary Tax Assessment Districts.
In 2023, the City of Winchester, in collaboration with the Virginia Main Street program, transitioned the administration of the program from city management to an independent nonprofit organization, initially called Winchester Main Street. Now titled, Friends of Old Town, this nonprofit is led by a volunteer Board of Directors that includes local business owners, property owners, residents, and other key community stakeholders.
Friends of Old Town serves as a liaison for downtown businesses and promotes the vitality of the Old Town Walking Mall through the administration of events.