Shepherd Hill Regional High School is located in Dudley, Massachusetts, United States.

It is a regional high school covering the towns of Dudley and Charlton.

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 original director Greg Stewart, and 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".