During its golden years, Canterbury was a highly regarded institution in the region. Compared to other private secondary schools in the Washington, D.C. metropolitan area, Canterbury was inexpensive and a much less stressful commute for students living in the Maryland suburbs of D.C. Canterbury was well known for both its athletic and academic programs. Unfortunately, the school did not sustain this reputation and enrollment began to decline. While some speculate that this was due to racist reaction to population changes in the area, the true reason for its decline remains unclear.