Various incarnations of a high school have been serving students in Westerly since shortly after the American Civil War.

[2] Three buildings in the first century (1870–1960) The first Westerly High School was built at 32 Elm Street in 1870.

[3] This led to an extremely crowded high school that, at some times, housed students in grades 7–12.

By 1987, State Street Elementary had reopened, which eliminated the seventh grade from the high school.

An elevator was added, the handicap ramp was redesigned, and a dumb waiter was installed in the auditorium.

Discussion was made about building a new school in Dunn’s Corners, but this idea was widely panned.

[4] Work at the high school included four new classrooms,[5] moving the office to a room on the first floor adjacent to the handicap ramp, replacing that office with a new expanded library,[5] and remaking the old library into the Guidance Department and Social Services.

[4] The high school also suffered from "turmoil"[6] and administrative instability in the later part of this era.

[6][7] In 2001, members from the Gilbane Construction Company argued that Westerly should build or expand its schools.

The property was bought in 2002, and the new Westerly Middle School broke ground in April 2004.

The high school’s corridors were renovated and select classrooms received new ceiling tiles.

Three classrooms were renovated into computer labs that allowed the remainder of technology teachers to conduct class there until construction was finished.

Tower Street closed as an elementary school that year and is now a community center.

The music program consists of a variety of courses including both academic as well as performing ensembles.