Post 21 was founded in 1919 and is one of the oldest and largest Posts in Virginia. 

A word about our namesakes "Conrad-Hoover" and a brief history of Post 21:
Most people think Conrad and Hoover are the same person, however, Robert Young Conrad was an attorney while Charles Loring Hoover was an artist. Both were soldiers and are honored for being first in Winchester — not in their fields, but on the battlefield because Robert Young Conrad and Charles Loring Hoover were the first soldiers to lose their lives by making the supreme sacrifice in World War I and II, respectively.

The Conrad-Hoover Post 21 of the Winchester American Legion on Berryville Pike honors the service and sacrifices made in wartime by Winchester and Frederick County men and women.

Robert Young Conrad,born in Winchester on Dec. 30, 1884, graduated from the University of Virginia law school in 1910 and became a partner in the law office of his father, Major Holmes Conrad. The younger Conrad was solicitor general of the United States under the Cleveland administration. 
Robert Young Conrad, an Army Captain, saw action in 1916 on the Mexican border with Company I, 116th Infantry Regiment of the 29th Division, known as the Blue and Gray Division. He was promoted to Captain and led his regiment into World War I. He was wounded on the Verdun front Oct. 8, 1918, and died the next day. Posthumously, Conrad was awarded the Distinguished Service Cross for “extraordinary heroism in action near Samogreux, France, on Oct. 8, 1918,” according to archive information. Although Conrad was buried at Verdun, a Cenotaph in Mt. Hebron Cemetery in Winchester was erected as his memorial.

Charles Loring Hoover, born in Winchester on April 3, 1920, graduated from Handley High School, Winchester. After basic training in 1942, Private Charles Loring Hoover was assigned to Battery C, 175th Field Artillery Battalion, 34th Division of the U.S. Army. 
“Charles Loring Hoover was a gallant soldier of the U.S. Army, who served with honor in defense of his country. " The courage with which he died is one of our greatest assurances of ultimate victory in this terrible struggle,” Army Chief of Staff Gen. George C. Marshall wrote in a personal letter to Hoover’s parents. Hoover was manning a gun post in Northern Africa during an enemy bombing raid on Nov. 29, 1942, when he was killed. A Grave Marker — a tall cross with his name on one side and “The Brave Die Young” on the reverse — indicates Hoover’s third and final resting place. His body was originally buried in Medjez-El-Bab, Tunisia, then moved to the American Cemetery in Beja, Tunisia. In 1948, his remains were finally returned to his family in Winchester.

The American Legion was originally named for Conrad in 1919, the year after his death, however, the American Legion Post was renamed the "Conrad-Hoover" Post in 1947.