The gap was named for Prince William, Duke of Cumberland, son of King George II of England, who had many places named for him in the American colonies after the Battle of Culloden. The explorer Thomas Walker gave the name to the Cumberland River in 1750, and the name soon spread to many other features in the region, such as the Cumberland Gap. In 1769Joseph Martin built a fort nearby at present-day Rose Hill, Virginia, on behalf of Dr. Walker's land claimants. But Martin and his men were chased out of the area by Native Americans, and Martin himself did not return until 1775.
In 1775 Daniel Boone, hired by the Transylvania Company, arrived in the region leading a company of men to widen the path through the gap to make settlement of Kentucky and Tennessee easier. On his arrival Boone discovered that Martin had beaten him to Powell Valley, where Martin and his men were clearing land for their own settlement – the westernmost settlement in English colonial America at the time. By the 1790s the trail that Boone and his men built was widened to accommodate wagon traffic and sometimes became known as the Wilderness Road.
Cumberland Gap was the center of a lot of activity during the Civil War and these are sometimes called Battle of the Cumberland Gap. In June 1862, Union Army General George W. Morgan captured the gap for the Union. In September of that year, Confederate States Army forces under Edmund Kirby Smith occupied the Gap during General Braxton Bragg's Kentucky Invasion. The following year, in a bloodless engagement in September 1863, Union Army troops under General Ambrose Burnside forced the surrender of 2,300 Confederates defending the gap, gaining Union control of the gap for the remainder of the war.