Before the widening of Massachusetts Avenue in the 1950s, Chester Square was an elegant park surrounded by a wrought iron fence and centered with a fountain. Among the notable women living there with their families was writer Anna Cabot Lowell Quincy Waterston (1812–99). She was a minister’s wife and the daughter of Boston Mayor Josiah Quincy.
Archeologist Harriet Boyd Hawes (1871–1945) was born and spent her childhood on Chester Square. After training at Smith College and joining excavations in Crete, she became the first woman to lead an archaeological expedition when she discovered the ancient town of Gournia on Crete.
In later years she also served as a volunteer nurse during the Greco-Turkish War and World War I.The South End Historical Society has worked to preserve the history and restore the buildings of the South End. The Society purchased 532 Massachusetts Avenue in the 1970s and occupies the parlor on the second floor which still has many original features. Architect Luther Briggs Jr. designed the building in 1860 for Francis and Zervia Dane. Realtor Betty Gibson (1907-1991) also helped revitalize the South End. In the 1960s she moved to 530 Massachusetts Avenue to demonstrate her commitment to the area’s renewal.