The Benedictine School was established in 1959 in the rural farming community of Ridgely, on Maryland's Eastern Shore. However, the school dates its history to 1891, when the Sisters of St. Benedict began a school for "young ladies and little girls" known as St. Gertrude's Academy. The school was operated continuously for more than sixty years until decreasing enrollment and few candidates for the novitiate forced the order to consider alternative uses for the property.

During the 1950's, the sisters recognized the need for a school to train and educate children and young adults with developmental disabilities - well before the general public's awakening to this fact. In 1955 the Sisters admitted a group of 12 girls with developmental disabilities on a trial basis. This pilot program's immediate success inspired them to continue with a full-time commitment toward children with developmental disabilities. The first class of 19 students (17 girls and 2 boys) started in September 1959. Since then, Benedictine has grown to accomodate nearly 200 children and adults.