The school district draws students from the towns of Toledo, Greenup, and Jewett.
Students just entering the district first attend the Cumberland Elementary School, which serves them from kindergarten to grade four.
The principal of the Cumberland High School is Kevin Meynard.
The district high school runs a series of clubs that range from a branch of the FFA and one that pressed towards environmental awareness to a National Honor Society, a varsity Scholastic Bowl team, and a woodworking club known as "Splinter Group.
[4] The Illinois Report card for 2022 designated the district a "Commendable School" with "no underperforming student groups, a graduation rate greater than 67%, and whose performance is not in the top 10% of schools statewide."