Highland was a part of the Olympic Conference, along with Muncie Southside, Connersville, Madison Heights, Huntington North, Noblesville, Carmel, and Jay County.

The Highlanders performed in full Scottish regalia, including kilts, plaids, and doublets.

The Highlanders also had a bagpipe corps within their ranks, one of only a handful in United States high schools.

As early as 1958, the Marching Highlanders began competing in the annual Indiana State Fair Band Day competition held in Indianapolis.

The Highlanders returned to the State Fair in 2004, and repeatedly proved their skills by earning the championship title in 2005, 2007, and 2009.