
The Woodrow Wilson School, now Dr. William W. Henderson K-12 Inclusion School, is located at 18 Croftland Avenue in the Ashmont neighborhood of Dorchester. The school was built in 1932 to accommodate increased development and population growth in the immediate area in the interwar period and was designed in a blending of Classical Revival and Art Deco styles, both popular at the time for such academic buildings. The building was named for Woodrow Wilson (1856–1924), the 28th President of the United States and was designed to comfortably accommodate 1,600 students. Architect, John Matthew Gray designed the building to conform to a plan drafted by the City of Boston in 1923 to standardize all new school construction down to the precise dimensions of windows and hallways. The permitted flexibility for hired architects was strictly on the exterior, where architects were free to create individual character in the designs of entryways, auditoriums, and exterior architectural styles and decoration. The entry of the Woodrow Wilson School depicts Art Deco motifs including lettering and inlaid carved panels over the door of a child reading and a child holding a globe. The school was renamed the Dr. William W. Henderson K-12 Inclusion School after the innovative educator of the same name.

