 He attended the School of the Museum of Fine Arts and Cooper Union from 1974–78, and he earned a B.F.A from Tufts University in 1988 and Judy Ann Goldman Fine Art in Boston.During the late 1970s, Armstrong became associated with the "Boston School" of photography, which included artists such as Nan Goldin, Mark Morrisroe and Jack Pierson.Their aesthetic was based on intimate snapshot portraits in saturated color.