In 1934, the present building that houses Jamestown High School began construction as part of President Franklin D. Roosevelt's New Deal.

Plans for a new high school had been considered as early as 1920 but problems with cost and siting kept the project from proceeding.

It also offers college-level courses via the Advanced Placement Program in a variety of subjects that allow students to receive university credit.

[7] In the fall of 2014, the Red Raider football team went to the NYSPHSAA Class AA Championship at the Carrier Dome in Syracuse, New York.

In 2014, the basketball program advanced to the state championship final, falling to Green Tech High Charter School.

In the late 1800s, classroom teachers utilized piano, guitar and whatever materials were available to them to provide music instruction in addition to the three "R"s.  Miss Ebba Goranson and her brother Arthur created our present day high school ensembles in 1924 with the establishment of the A Cappella Choir, Orchestra, and Band.

[9] The modern Jamestown High School band program began in 1924 under the direction of Arthur Goranson.

In 2000, the band was named Grand Champion International at the North American Music Festival Competition in Myrtle Beach, South Carolina.

The band traveled to Disney World to participate in the Electric Light Parade in the Magic Kingdom in 2012 and 2014.

In December 2019, the band traveled to Disney World to perform in the Magic Kingdom's New Year's Eve Parade.

Other directors of the band include: Delbert Vossberg (1948–1953); Charles Jacobson (1953–1968); Cecil Adams (1968–1969); Frank Smeragliuolo (1969–1970); Jeffrey Corbin (1970–1980); Lou Deppas (1980–2000); Gary Kurtis (2000–2001); Keith Hall (2000–2001); Cathy South (2001–2002); Cory Derrenbacher (2002–2005); Jeff Hoffman (2002–2003); Jamie Sigler (1998–2006); James Stephens (2005–2006); Marc Lentsch (2006–2010); and Meghan (Bolling) Murray (2006–present).

[11] In 2018, the band successfully completed their season with another win in the Large School 2 division with their show "Canon ".