Older than the new City of Roanoke developing to its south, Gainesborough ("Old Lick") was growing as a racially-diverse neighborhood that was the center of the African-American community by the 1890s. Businesses serving the community were located on Gainsboro Road, from Gilmer Avenue north to Rutherford Avenue, and along First Street (later Henry Street) north of the railroad tracks. Doctors, lawyers, ministers, educators, industrial laborers (mostly at the railroad), domestic workers, and self-employed residents lived together as a cohesive community where residents looked after one another.
By the early 1920s, the neighborhood became a self-sustaining African-American community. Strong churches, schools, social institutions, and professional and commercial services developed to serve the growing black population, otherwise denied services in the segregated South. Consequently, skilled black leaders emerged to become locally and nationally influential in social, civic and business affairs.
From the early 1900s through the 1960s, there was a vibrant business district and various social activities for the black community on Henry Street and Gainsboro Road. The area bustled with restaurants, hotels, and a theater; insurance companies, law offices, financial institutions, and medical offices/pharmacies; barbershops,
undertakers, tailors, dry cleaners, and a shoemaker; as well as many other businesses. The weekly Roanoke Tribune was first published in 1939 from Gilmer Avenue. Ten black-owned grocery stores operated throughout the neighborhood, but there were also white-owned grocery stores, including one in the building now restored as an office at the corner of Gilmer Avenue and Jefferson Street.