The town's mayor presented a capital improvement plan for the school in 2002, but funding was limited and residents questioned the project's first phase plans for a wellness center (athletic complex).

Additionally, the Transitional building is home to the Cumberland School Department administration.

The campus finished major renovations known as CHS 2010 at the end of the 2007–2008 school year.

This project was designed to create a 21st-century learning environment on the campus of Cumberland High School.

Cumberland High houses departments in English, Mathematics, Sciences, History, Languages, Special Education, and Fine Arts Extracurricular activities The school hosts approximately 28 clubs and co-curricular activities as well as over 20 sports for girls and boys.

There is also a Robotics Team that traveled to Atlanta in 2007 to participate in the VEX World Competition.