Olean High School's original building was constructed in 1882. Eventually the building became out of date and overcrowded, creating potential fire hazards. It was eventually taken down in the spring of 1935, with only the gymnasium being spared. Due to economic hardships after the War, it wouldn't be until 1937 that the new building was constructed. Back in that time, the new school had the most modern labs and library, as well as a radio speaker system with receivers in each room, allowing the principal to make daily announcements.
In 1997 the building was added to the Registry of Historic Sites.