The last day for Orlando High School was June 6, 1952. With more than 1,200 students, the school had outgrown the blond-brick 1926 edifice on Robinson Street. The Orange County Board of Public Instruction had built two new high schools that would open in the fall, and Orlando High School was to become Howard Junior High. The students were gone that Friday morning, and Principal William R. Boone was working at his desk. He had been principal of the school for most of the years it had been open, and students and staff said he was the heart of the school.
But as he sat as his desk, Boone suffered a fatal heart attack.
In tribute, William R. Boone High School was named after him. It opened that fall alongside Edgewater High School. Today, a plaque honoring Boone hangs next to the front doors of his old campus, now known as Howard Middle School Academy of Arts.
“There was so much history in that building,” said Sara Chisari, who taught physical education at Howard for more than two decades starting in the late 1970s. “I felt like I could feel the footsteps and the voices of those who had been there.”
Orlando High School was a monument to be proud of, with six columns in the front, decorative masonry and a marble cornerstone. A gymnasium and cafeteria had been added over the years, and two lions today guard the front entrance. Students there competed academically and athletically statewide, and participated in debate, an aviation club, football, basketball, spelling bees and plays. They joined honor societies and went on to lead distinguished lives. Graduates included astronaut John Young and actor Buddy Ebsen.
But it wasn’t the first Orlando High School, which first graduated 11 students in 1892. Those students learned on the second floor of a multi-grade school building located where the SunTrust Center stands downtown today (pictured left).
And in 1886, Jones High School was established for Orange County’s black students. The school moved to a stately red-brick building on North Parramore Avenue in 1921. It was renovated and reopened as the Callahan Neighborhood Center in 1986.
Even a few decades ago, the classrooms at the former Orlando High School still retained transom windows and the original layout. In 2001, the school was modernized with a comprehensive renovation that expanded classrooms and added a new building. 
Old letters reading “OHS” are still visible near the roofline on the southwest corner of the school.
The school’s second name came from C.E. Howard, chairman of the board of trustees in 1926, when the cornerstone was laid. The new school quickly developed its own traditions as the “Home of the Rangers,” and a student was awarded the school Citizenship Cup each year from 1953 to 1996.
In 1987, the school was converted to a middle school, and in 2011 was designated as a magnet school. In 2018, it became a zoneless magnet. “It was a very special place to work,” Chisari said.