- December 9, 1775: The Battle of Great Bridge
- December 11–15, 1862: In the Battle of Fredericksburg (pictured), Union troops cross the Rappahannock River under fire into Fredericksburg and face the first major urban combat of the American Civil War.
- December 16, 1907: The Great White Fleet departs Hampton Roads to begin its circumnavigation of the globe, heralding the rise of the United States as a world naval power.
- December 20, 1606: A fleet of three ships, Susan Constant, Godspeed, and Discovery, sets sail from England bound for the New World to establish the Colony of Virginia, led by Captain Christopher Newport.
- December 26, 1811: 72 people, including the governor, are killed in the Richmond Theatre fire, the worst urban disaster in the United States to that point.