Template:On this day/May 29
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- 1923 – Albemarle County Clerk of Court William L. Maupin dies.
- 1927 – From the Jefferson Theater, Daily Progress Station WKBG went on the air - becoming the first broadcast station ever to be brought to Charlottesville.
- 1952 – Deputy Sheriff Deputy Thomas Wolfe was mortally wounded in a shootout with a suspect accused of shooting into a neighbor's home for two consecutive days. Wolfe's partner shot the suspect. Wolfe succumbed to his injuries two weeks later. The suspect died on the day of Wolfe's funeral.