(Circa 1947 photo by William P. Gottlieb, via Wikipedia)
His family (both of his parents and all four grandparents) were from Hillsborough, and his grandparents lived in or near the town their entire lives. In the early 1920s, his mother sent him to Hillsborough to live with his father's parents, Jobe L. and Elizabeth "Lizzie" A. (Craig) Strayhorn. His mother's parents were George and Julia Craig.
Strayhorn learned to play music on his grandmother's piano, he also played 78rpm records on her Victrola phonograph
. Years later, Strayhorn told an interviewer that his grandmother was the primary influence during his early years, and that her house felt like his first real home.
He had three brothers; one of the brothers, John Francis Strayhorn
, was born in Hillsborough on October 19, 1923. Strayhorn returned to Pittsburgh to live with his parents while still in grade school, sometime around 1923 to 1925.
(Strayhorn's WWII draft card)
His paternal grandparents, Jobe and Elizabeth "Lizzie" Strayhorn, owned and lived on a property in West Hillsborough, at the south west corner of Hillsborough Street and Margaret Lane (Lot 232). Jobe worked at one (or both) of the local cotton mills (the Eno and the Bellevue) as a laborer most of his life. Lizzie Strayhorn died in June 1923. Jobe Strayhorn sold the family property in March/April 1925. He died January 22, 1951 at Lincoln Hospital in Durham. They are both buried in Maplewood Cemetery in Hillsborough.
His maternal grandparents, George and Julia Craig, were also from Hillsborough. They lived at various times west of Hillsborough (in what was once called Chaseville), and on the south end of east Hillsborough, near the Nash-Kollock school building, likely in one of the former slave dwellings to its east. George died in August 1921, and Julia died in August 1932. They are also buried in Maplewood Cemetery in Hillsborough.