The current Hillside High School is the third of its name, with a history going back to the 1880s when Durham opened its first public graded school for African Americans. The name Hillside dates from 1922, when students moved to a new building on Umstead Street at first called Hillside Park High School because of its location uphill from the public park.

Hillside High remained there until 1950, by which point it had far outgrown its accommodations. The city school board made a swap sending the high school to the newer Whitted Elementary building on Concord Street and the elementary school to Umstead. The schools names went with the student bodies.

Hillside remained on Concord Street until its new 63-acre campus opened in 1995. Remodeled and enlarged twice, Hillside has an official capacity for 1,535 students in 290,000 square feet of building space.