With Louis Armstrong as inspiration, Herb Pomeroy chose the trumpet as his instrument. By age twenty-five, he had performed with Charlie Parker, toured with Stan Kenton and Lionel Hampton and recorded with Serge Chaloff. Herb Pomeroy became known as a musician's musician, a leader in big band jazz, an improviser of uncommon stature, a legendary educator at the Berklee College of Music for forty-one years and founder and director of the Festival Jazz Ensemble at MIT for twenty-two years.
By the age of twenty-two audiences already had identified Pomeroy as an exceptional trumpet player. He left Harvard University after one year to join the legendary Charlie Parker Quintet. Herb also received praise as composer, arranger, soloist, and section player with the bands of Lionel Hampton and Stan Kenton and then established one of the most formidable bands in the world - the Herb Pomeroy Big Band.