The Richard Montgomery Jazz Ensemble is one of eight performing ensembles at Richard Montgomery High School in Rockville, Maryland (a suburb of Washington DC). The ensemble consistently receives critical acclaim at local, national, and international levels. It regularly participates in the Blues Alley Big Band Jam in Washington D.C. and the Mid-Atlantic Jazz Festival. In 2009, the band performed in Yilan, Taiwan for the Yilan International Arts Festival (one of the few American bands to do so). In addition to these notable engagements, it has performed on local television and for events around the Washington DC area.

The Richard Montgomery ensembles have performed at: The Eastern Division National Association for Music Education Eastern Division Conference, The Annual Blues Alley Big Band Jam, the East Coast Jazz Festival, The Mid-Atlantic Jazz Festival, The Maryland State Band & Orchestra Festival, and DAR Constitution Hall. The National Association for Recording Arts and Sciences (NARAS) has designated the program as a Grammy Signature School. Students in the program consistently represent Richard Montgomery High School in Montgomery County Honors Ensembles, Maryland All-State Ensembles, All-Eastern Ensembles, and All-National Ensembles.