Shepherd Hill was established in 1973. The school formerly included grades 7–12, but in 2000 Dudley and Charlton opened separate middle schools and the school is now restricted to grades 9–12.
Shepherd Hill has a highly decorated Marching Band, Winter Percussion, and Winter Guard. The Shepherd Hill Band programs hold near “Dynasty” status among New England music programs, winning numerous titles in MICCA, NESBA, and USBands competitions across the northeast. Following on the heels of Shepherd Hill band legends Cindy Snow, James Flynn, and Dave Macuga, new director and alumnus Thomas Wilson (‘06) aims to carry on the tradition for the next generation of Dudley and Charlton musicians.
In addition, Shepherd Hill has three competitive show choirs: the mixed-gender "Fantasy", the all-female "Illusion", and the all-male "Testostertones".[5] The school is recognized as one of the first to have a show choir in New England, having established the group in 1984.[6] The program also hosts an annual competition the first weekend in February.[7]