Chesapeake is Virginia's second most populous city — covering 340 square miles across seven unique boroughs including South Norfolk, Great Bridge, Greenbrier, and Deep Creek. Deep in the 757, Chesapeake sits at the southern edge of the Hampton Roads region and has one of the most distinctly Southern urban cultures in Virginia. The Chesapeake Bay shapes everything here — from the seafood culture to the pace of life to the deep community roots that have kept Black families and businesses rooted in this city for generations. These businesses represent the South Side's most committed entrepreneurs.