Portland High School was first established in 1821 in an Exchange Street building. In those early days, the English High School for Boys was housed in several different buildings. In 1850 a High School for Girls was built on Chestnut Street behind the present Portland High School. In 1863 the school moved to its present location on Cumberland Avenue. That building is now the middle wing of today's school. The most memorable feature of that Portland High was a brick wall which ran through the middle of the building from the basement to the roof. It served to separate the girls from the boys. Eventually the wall was removed, but the remnants of it can still be seen in the basement.

Portland High School was the third public high school to be established in the United States, and today remains as the second oldest continuing high school in existence. Portland High School was a pioneer in secondary education in the nation and has long been a leader in our state.

Thomas B. Reed, who was the Speaker of the United States House of Representatives; Admiral Robert E. Peary, who discovered the North Pole; and John Ford, who was a giant among movie directors, are only a few of the notable graduates. The new addition to the school was opened in 1989. It includes a new athletic facility, a new cafeteria, several new classrooms, and the finest theater/auditorium in the city.
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