Born in Ireland, John Handley immigrated to America in 1850 and studied law at Columbia University, eventually becoming a judge. Upon his death in 1895, Handley bequeathed $250,000 to the town of Winchester, VA. Funds were used to construct Handley Library, Frederick Douglas School, and Handley High School, all three of which are now listed on the National Register of Historic places. Prior to establishing Winchester’s school system, Chairman of the Handley Board of Trustees, R. Gray Williams, implemented a progressive philosophy as a guide and in deference to Handley’s original proposal to give Winchester a park, the Board hired John Charles Olmsted (1859-1920), the country’s leading landscape architect, in 1916 to plan the 72 acre Handley school and playground site. Soon after, Walter Roy McCornack (1877-1961), official architect for the Cleveland School Board from 1914-1925 and best known for his schools and public housing projects, was hired to design Handley High School on the eastern 40 acres of the 72-acre plot of land.
The resulting historic designed landscape is reminiscent of Frederick Law Olmsted, Sr.’s, formal Beaux Arts design for the Columbian Exposition of 1893 (Chicago World’s Fair) and includes a formal design for all areas adjacent to buildings with a natural, park-like area on the perimeter. The football stadium and track are located in front of the school in an area known as the Handley Bowl. Between the Bowl and Valley Avenue to the east is a double allée of trees flanking a grassy mall (similar in character to the mall in Washington, D.C.) terminating in a large open lawn used as a football practice field. On the north and south side of the formal mall are informal natural areas of trees on small rolling hills and valleys. Along with being associated with a master craftsman, the school’s grounds host several significant horticultural features. Maple trees on the north side of campus along Handley Boulevard were planted as memorials to those Winchester soldiers that died in World War I. Japanese cherry trees from the Jefferson Memorial in Washington, D.C. were obtained and planted by Principal Dr. Garland R. Quarles. John Handley High School, including its grounds, was nominated by the Handley Board of Trustees and listed on August 14, 1998 at the state-wide level of significance in the National Register of Historic Places as the first and only privately-endowed, public high school in Virginia and one of only four schools in the state associated with John C. Olmsted.