Stilesboro was incorporated in 1866 and retained that distinction until 1995. It was named for Savannah attorney William Henry Stiles, who served in Congress and the Georgia House of Representatives.

A high school was established here in the late 1850s and the community raised funds and completed the present structure in 1859. It was the center of the community and during the Civil War was used for sewing Confederate uniforms. Though it is likely apocryphal, a legend persists that in May 1864 Sherman spared the Academy due to an interior inscription: Deo ac Patriae [God and Country]. [I say it’s likely apocryphal because there’s a story like this for nearly every surviving antebellum building in the South].

The Stilesboro Improvement Club, a woman’s benevolent society, lobbied to save the old Academy when a new school was built nearby, and has owned the building since the school closed in 1939-1940. Formed in 1910, the club, at the suggestion of Miss Campie Hawkins, began holding an annual chrysanthemum show in 1912. The Stilesboro Chrysanthemum Show continues to be a popular event, 108 years later. It has taken place every year, except during the Great Influenza (1918) and World War II (1942).

The Etowah Valley Historical Society notes that research on the history of the Academy is incomplete.