The first colonists arrived in 1607 when English Captain Christopher Newport landed at Cape Henry, today’s City of Virginia Beach, an event now called the “First Landing.” However, his party moved on, in search of a more defensible area upriver, mindful of competitors such as the Spanish, who had built a failed settlement on the Virginia Peninsula known as the Ajacán Mission.
After exploring the James River, they established the first successful English colony in the New World on Jamestown Island on May 14, 1607. But the low, marshy site proved unhealthy and most of the colonists died, before a new Governor, Lord De La Warr (Delaware) arrived with John Rolfe, who would establish the Virginia tobacco industry.
The harbor and rivers of Hampton Roads were immediately recognized as prime locations for commerce, shipbuilding and military installations, with the fortifications at Old Point Comfort established as early as 1610, and Gosport Navy Yard (later Norfolk Naval Shipyard) in 1767. The decisive battle of the Revolution was won at Yorktown in 1781, and the first naval action of the War of 1812 took place in Hampton Roads, when a Royal Naval vessel was seized by the American privateer Dash. Later the entrance from Chesapeake Bay was equipped with new fortifications (Fort Monroe and Fort Wool), much of the building work being supervised by a young military engineer Robert E. Lee.
During the American Civil War (1861–1865), the historic Battle of Hampton Roads between the first American ironclad warships, the USS Monitor and the CSS Virginia, took place off Sewell’s Point in 1862. The battle was inconclusive, but Union forces later took control of Hampton Roads, Norfolk, and the lower James River, though they were thwarted from venturing further upstream by a strong Confederate battery at Drewry’s Bluff. Also in 1862, Fort Monroe was the launching place for Union General George McClellan‘s massive advance up the Virginia Peninsula, which almost reached the Confederate capital Richmond, before the Seven Days Battles forced him back. In 1865, as the Confederacy was near collapse, President Abraham Lincoln met with three senior Confederates at Hampton Roads in an unsuccessful bid for a negotiated peace.
Some former slaves had been camped near Fort Monroe, where they were declared to be Contraband of war, instead of being returned to their former owners. Booker T. Washington was among the freedmen who attended the local school, which evolved into the present-day Hampton University.