HHS is in the southeast corner of Madison County and is part of Highland Community Unit School District 5.

The 1600 block of Lindenthal Avenue housed Highland High School classes beginning in the fall of 1935.

The building was built in part to the National Recovery Act and need for a new public school.

In 1974 it was determined that the Lindenthal campus was no longer a viable location for HHS and the Capitol Development Board offered a grant to the Highland Community School District.

Highland High School would begin classes on Troxler Avenue starting in the fall of 1976.