The Governor Livingston Highlander Band was under the direction of Dan Kopcha since the early 1970s. In 2007 Kopcha announced his retirement and the band has subsequently been under the direction of Nicholas O'Sullivan, himself a Governor Livingston alumnus and former Highlander Band member. The band is extremely competitive and has been recognized with many awards. One of the earliest competitive wins was the 1972 award of the Governor's Cup at the Festival of States in St. Petersburg, Florida. The band competes against other bands associated with an organization called Tournament of Bands (TOB). TOB is organized into regions called "chapters", with the Highlander Band being in Chapter X. The championship competition is known as the Atlantic Coast Championship held each November. The Highlander Band has won many awards in TOB such as 28 chapter championships. Every four years, most recently in 2018, the band travels to Scotland to perform in Ancrum, Stirling and Edinburgh.
