Gainsboro Historic District & Henry Street

Gainsboro was founded in 1835, making it Roanoke's oldest community. The physical district you walk today — 202 contributing buildings, three churches, a library, a theater, a hotel — was built primarily between 1890 and 1925. By then, Gainsboro had become what locals called Roanoke's Black Wall Street. Henry Street was the entertainment heart. Louis Armstrong, Duke Ellington, and Ella Fitzgerald performed there. Urban Renewal demolished 1,600 homes, 200 businesses, and 24 churches. What survived was listed on the National Register of Historic Places in 2005. The Henry Street Historic District is separately listed. A self-guided walking tour is available. You walk what endured.