The Cavaliers bring with them a deep tradition of excellence under the capable leadership of band director, Paul Hess, starting in the 1970s. Creating great music for Middletown was a family affair for Paul and his wife Joyce, who was the band director at Redding Middle School for 33 years.

In the 1981, Bob Musser became the band director, but turned the program over to Jonathan Wittman, who was the assistant director and chorus teacher, after just one year. During Jonathan’s tenure as band director, the marching band joined the Tournament of Bands competitive circuit and began placing at the Atlantic Coast Championships (ACCs). Dave Harris joined the program at this time as the assistant band director and would eventually become the band director after Jonathan’s departure in 1986. Due to a small school population, it was decided that Dave would be the only music teacher. Highlights from the band’s history in the late 1980s included the band’s continued participation in the Tournament of Bands and New Castle County Band Festival as well as Middletown’s “home show” that ran for a decade until the number of bands attending made the competition too difficult to run. Another highlight from the 1980s was the band’s performance of “Dear Old Donegal” in the New York Saint Patrick’s Day parade; a tradition that would last nearly 20 years.

The 1990s heralded a change for the Cavaliers. The band did fewer competitions but many more football games as the team began to win state championship.  The Magnificent Seven became the football team’s theme song at this time as well. As the population of Middletown and Middletown High School grew, so did the size of the band. The band began to make overnight trips to include performances in Myrtle Beach, Toronto, Williamsburg, Atlanta, and Orlando. The band attended its first Bowl game in Tampa, Florida in which they performed in a concert, a parade, and at halftime with other high school bands.

In 2009, Dave Harris retired after 30 years of teaching high school band. Matt Pagel became the next band director and in the fall of 2009 took the band back to Atlantic Coast Championships once again. Our current band director is Brian Endlein, former director at William Penn High School.

This ensemble has been a finalist at the Tournament of Bands Atlantic Coast Championships on numerous occasions with their most recent placement in 2009. The Cavaliers have received awards for Best Drum Major, Percussion, and Colorguard throughout their many years of performance. The band has been graced with many talented members, many of which participated in All-State and All-Eastern ensembles. Many members have gone on to become music educators and perform with many prestigious ensembles to include The US Marine Corps Band. The ensemble has been a finalist at the Tournament of Bands Atlantic Coast Championships on numerous occasions most recently; the Cavaliers attended ACCs in 2009.