Winston Hall was on East Main Street where the Bank of Clarke County driveway is now located. Built in 1881 by Siz Daingerfield, a black barkeep, it was named for singer, Jenny Winston. Upstairs was the largest meeting hall in the town and was used for entertainments and even school graduations; down stairs was the saloon. From 1920 until 1938, American Legion Post 41 used Winston Hall for its meetings.

Griffin Taylor operated Winston Hall for years with a clothing store below. Later, owners James W. Gaver and Fred Morris sold farm machinery and cigars. From 1922 to 1939, the upstairs portion of the building was rented by the Virginia National Guard and served as the armory for Headquarters Company of the 91st Infantry Brigade. In 1957, the building was purchased by the Bank of Clarke County and demolished in 1962 to expand the bank building and parking lot.

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