This article is a date listing important events for the year 1916.
- June 27 – more than 75 members of the Monticello Guard, Company D, 1st Regiment departed Charlottesville to join other Virginia Guard groups, totaling nearly 4,000, heading to the border lines of the Mexican Revolution. The guardsmen returned home in late that year.
- August 1 – Charlottesville became a city of the first-class when it undertook annexation of a large portion of surrounding suburbs, which more than tripled its size. Subsequent annexations took place in 1939, 1963 and 1968. The Virginia Constitution of 1902 defined first-class cities as those having a population of 10,000 and requiring a city's Legislative government consist of a two chamber city council composed of 4 Alderman and 8 Councilmen. The university successfully opposed attempts to include it in the political boundaries of Charlottesville.
- September 20 – 1916 election was special election held for a new city council under the form of Legislative government prescribed by law for the cities of the first class.
- October 31/ November 1 – The entire Commonwealth of Virginia went dry at midnight – three years before national prohibition began.