Roxbury Latin is the oldest school in continuous existence in the nation. Founded in 1645 by John Eliot, Roxbury Latin is a day school for boys, located on its third campus, a sixty-six-acre lot with rocky outcroppings. Influenced by the country day school movement, it moved from central Roxbury in 1927 to a suburban location with room for playing fields. Notable for its central core by William Perry, the slate-roofed brick building (1926–1927) wraps gabled wings around a U-shaped courtyard dominated by a giant elm. Its Classical Revival vocabulary was widely borrowed, as seen in the cast-stone Doric pilasters, twelve-over-twelve colonial windows, and an Italian loggia and octagonal tower. Subsequent wings all attach to the core, including the modern-style Albert Gordon Field House (1957, Hugh Stubbins and Associates) and the Ernst Wing (1966, William F. Halsey). Best known for their Colonial Williamsburg designs (beginning 1928), Perry, Shaw and Hepburn also completed more than fifty designs for schools, colleges, and universities.
Roxbury Latin increasingly sought consistency with Perry's design, screening Stubbins's wing with plantings and rejecting Halsey's first design in favor of a more referential wing. William D. Buckingham, current architect and planner, characterized the change from Stubbins to Halsey as movement from “stark confrontation to grudging accommodation.” Buckingham designed wings in a postmodern style sympathetic to Perry—Mary Gordon Building (1988), Smith Arts Center (1993), and Bauer Science (1998)—and oversaw the 1999 gutting of the Perry core for a technology center. Buckingham's Athletic Center addition (2000) completely masks the campus facades of the unpopular Stubbins wing.