[4] Opening in 2005, Casco Bay High made Portland the first city in the United States to offer Expeditionary Learning from kindergarten to 12th grade.

[9] Every student at Casco Bay High School is assigned to peer groups known as crews designed to facilitate inclusivity and faculty mentor relationships.

To date, all Junior Journeys have been executed in association with Habitat for Humanity in Biloxi, Mississippi, Almost Heaven, West Virginia, and Rockaway, New York.

During the trip, which is entirely funded by the students' own fundraising efforts, the junior class spends time volunteering, team building and bonding, and taking in local culture, history, and landmarks.

Derek Pierce was Casco Bay's founding principal, serving since the school's opening in 2005 through the 2023-2024 academic year.

[10][11] In 2014, he won Nellie Mae's Larry O'Toole Award for exhibiting "great leadership through innovation or courage in moving student-centered approaches to learning forward".