Woodruff High School is historically significant for its long association with education and civic activity in Woodruff during the first half of the twentieth century, and is also architecturally significant as an outstanding and well-preserved example of the work of prominent Greenville architects Frank H. and Joseph G. Cunningham. Woodruff High School was built in1925 at a cost of $50,000. It replaced the original high school, which was built in 1908 on East Georgia Street. The Cunningham-designed building housed the high school until a new facility constructed outside of downtown opened in September 1953. It subsequently served as the junior high school and, in the late 1960s, was home to the elementary school. In 1978 the City of Woodruff acquired old Woodruff High School and adapted it for use as its city hall and police headquarters. The two-story building’s form is a modified “H” plan with a three-part center section, two perpendicular wings, and a flat roof. It occupies nearly 30,000 square feet, including a 600-seat auditorium. Exterior masonry walls are covered in gray stucco. The modern windows are a metal awning variety. Moldings and Gothic arches ornament the exterior, particularly at the entrances. Woodruff High School exhibits many of the defining decorative characteristics of the collegiate Gothic style. Popularized after the First World War, the collegiate Gothic style was noted for recessed entrances framed by pointed arches. Other defining elements include brick exterior walls with raised moldings, large window bays with multi-paned sashes, and a flat roof with parapet. Woodruff High School, as originally built, exhibited all of these features, plus small quoin-stones, drip moldings with bosses and a tablet molding at the main entrance. Listed in the National Register October 18, 2006.