Located along North Main Street (US Route 29) in a mostly residential area in the Pittsylvania County town of Chatham, Gilbert’s Restaurant was constructed ca. 1945 by the Reverend Robert Gregory Gilbert as a gas station, grocery and general store, tourist home, and café serving Black citizens. Built in a time of social change in the years following World War II, Gilbert’s Restaurant historically served as a local haven and a harbor for Black entrepreneurship, women’s economic freedom, civil rights, and racial justice, and it remains emblematic of Black entrepreneurs across the American South who sought to unroot the “separate but equal” justification of Jim Crow-era racial segregation. The business thrived as a one-stop shop for Black men and women who otherwise had doors closed to them in a racially segregated South. As a restaurant and tourist home, Gilbert’s hosted everyone from Black teachers to famous musicians and entertainers and was home to notable meetings of civil rights organizations and NAACP attorneys. The nominated boundary also includes the Gilbert family home, a Craftsman-style residence located about ten feet north of the restaurant.