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The second building financed by Ann and John Hillins, Main Building was envisioned by Charles Lewis Cocke as "one of the most elegant edifices in the South." Original plans for the structure included three floors of balconies along the entire front and ends supported by Ionic columns and crowned with a cupola, but this image remains only on diplomas and catalogues of 1860. Construction of Main began on April 17, 1861, the day that Virginia seceded from the Union, and scarcity of materials and labor during the Civil War delayed completion of the building for eight years. Sections of Main were used as they were completed, prompting students to name to skeletal structure "The Wilderness."
In addition to serving as a student dormitory, Main's left side contained a chapel that rose through the first and second floors, while the basement served as a dining hall until 1890. After completion of Bradley Chapel in 1883, Main's chapel was converted to a parlor, reading room, and library. For close to nine decades, the right side of Main Building's first floor housed the office for Hollins presidents, from Charles Lewis Cocke to John Everett in 1956. This area now contains admissions offices, and the Green Drawing Room, used for receptions, readings, and lectures, occupies the former chapel space. The Cocke Sitting Room, designated in 1959 as a memorial to Charles Lewis Cocke, is furnished with original Cocke family furniture and features the parlor fireplace mantel from the Botetourt Springs Hotel. The upper floors continue to serve as student residence halls.
Hollins College Quadrangle. National Register of Historic Places designation report. Washington, DC: U.S. Department of the Interior/National Park Service, 1974.
Meredith, Molly. "An Historical and Architectural Guide to Hollins College." M. L. S. thesis, Hollins College, Roanoke, VA, 1997.
Niederer, Frances J. Hollins College: An Illustrated History. Charlottesville, VA: University Press of Virginia, 1973.
Vickery, Dorothy Scovil. Hollins College, 1842-1942: An Historical Sketch. Roanoke, VA: Hollins College, 1942.
Whitwell, W. L., and Lee W Winborne. The Architectural Heritage of the Roanoke Valley. Charlottesville, VA: University Press of Virginia, 1982.