Therefore, it was rebuilt in the same location with a similar footprint painted in the classic North Clackamas Grey and Tan.

The school operated for two years in trailers built in the current track and field areas.

[2] The school's first mascot, the Maroon, fell into disfavor with students because of its similarity to the word "moron.

[6] In 2008, the JC Lillie Center for the Arts, the school's performing arts center, underwent a major aesthetic and structural renovation, which included a redeveloped entrance and courtyard, remodeled auditorium, and a notoriously faulty sound system.

[7] In June 2018, the school's main campus was demolished to make space for a new academic building.

Since 1996, Milwaukie High School has annually hosted the nationally recognized [10] Living History Day.

On this day, thousands of veterans are welcomed into the school to help educate students about past wars and provide first-hand accounts of military experiences.

[14] The Pony Prancers dance team won first place in their division at the OSAA State Championships in 1986, 1996, 2011, 2012, and 2016.

[citation needed] Milwaukie High School holds the title of the oldest Thespian Society Troupe in the state of Oregon.