Originally built as the J.A. Whitted Elementary School in 1935, the school building located between East Lawson, Formosa, and Concord Sts. became Hillside High School around 1949, when the school board had Hillside and Whitted switch buildings to facilitate expansion. The original structure, with its impressive two-story entryway, was designed by George Watts Carr, Sr. Around the time that the school became Hillside, wings were added to either end of the original structure; these included an auditorium, cafeteria, autoshop, classrooms and a gymnasium.
The oldest portion of the school was built in 1922 as Hillside Park High School, the first high school for black students in the city. Its architect, Milburn, Heister and Company, designed many school buildings during the era, including what is now Durham School of the Arts, and notable Durham buildings including the 1916 courthouse and the Durham Auditorium – now the Carolina Theatre.