Dudley Square has long stood as a gateway to Roxbury and the surrounding southern neighborhoods of Boston. During the colonial period, when the delicate Roxbury Neck Road, now Washington Street, served as the only land bridge between Boston and mainland Massachusetts, Dudley saw all traffic into and out of the city. During the Revolutionary War, colonists fleeing British occupied Boston, travelled through what would later become known as Dudley Square in order to reach neighboring safe havens. However, even after the Back Bay and the South End were filled in, and other highways opened into Boston’s downtown, Dudley remained a transportation hub.


