Recognition of the military value of the site dates from its earliest exploration under the command of Captain Christopher Newport in 1607. Newport's expedition reached the entrance of the Chesapeake Bay April 26, 1607, and landed at Cape Henry. Parties were immediately dispatched to explore the southern shores of the bay for suitable anchorage.
After several unsuccessful attempts, they rowed to a point of land where they found a channel and "sounded twelve fathoms." This put them in such "good comfort" that they named the point "Cape Comfort" and later "Old Point Comfort" to distinguish it from New Point Comfort, at the mouth of Mobjack Bay, some 20 miles to the north.
The three ships of Newport's expedition, Godspeed, Susan Constant and Discovery, reached Point Comfort April 30, 1607. Upon arrival, the Englishmen spotted a band of Native Americans running along the shore, so a party landed. After the first timid encounter, the sailors were invited to visit the village of Kicotan (now known as Kecoughtan and the site of a Veterans Administration Hospital and Navy Cemetery).
From this point Newport's men made further expeditions that resulted in the establishment of the first permanent colony in America at Jamestown.
On Oct. 3, 1609, Captain James Davis arrived from England with 16 men in the pinnace (a light sailing ship) Virginia. Under the guidance of Captain John Radcliffe, these men (aided by a detachment from Jamestown) built a Fort at Point Comfort.
When completed, the structure was named "Algernourne Fort" in honor of William de Percy, the first Lord Algernon, who had come to England with William the Conqueror in 1066. At first, the Fort was a simple earthwork, but by 1611 it was a well-manned and sturdy fortification. Within its walls were a magazine, seven heavy guns, several smaller weapons, a storehouse and quarters for the 40-man garrison under the command of Captain Davis (Captain Radcliffe had been killed by Natives while on a trading expedition up the York River). In 1612 the Fort was destroyed by fire.
Captain Davis immediately attempted to rebuild the Fort, but because of sickness and lack of provisions, little progress was made. During an inspection of Port Comfort in 1621, it was reported that there were "practically no fortifications capable of resisting a foreign enemy."
By 1630 a new Fort was planned and command of the project was given to Captain Samuel Matthews. In 1632, he reported that the Fort was completed. Because of a lack of maintenance, the Fort soon fell into decay and was finally abandoned in 1665.
Dutch raiders ventured up the James and burned or captured a number of vessels laden with tobacco. As a result, a force was returned to Point Comfort, and the fortifications were rebuilt. In 1667 this Fort was destroyed by a storm described as "...the most Dreadful Hurry Cane that ever the colony groaned under...The waves carried all the foundation of the fort at Point Comfort into the River and most of our Timber which was very chargeably brought thither to perfect it."
Since the very foundations of the fortifications at Point Comfort had been destroyed, little was done in the way of fortifying them between 1667 and 1728. It was not until Spain declared war on England in 1727 that work on the fortifications at Point Comfort began in earnest. The new Fort was named in honor of the reigning king of England, George II. In 1749, Fort George was destroyed by a hurricane.
Fort Monroe is the latest of at least four fortifications on a piece of land known as Old Point Comfort. The first example was a wooden stockade called Fort Algernourne. It was constructed by Jamestown colonists in 1609 but accidentally burned to the ground three years later. Two other colonial forts were built in the 18th century, one called Fort George and the other without any designation. Both were destroyed by storms. Thereafter, the garrison consisted of one man, charged with the "care of the ruins remaining at Old Point Comfort." To combat the boredom of his lonely occupation, the caretaker began exhibiting a light at night for the benefit of passing ships. In 1802, a lighthouse (still in operation) was built on the point. During the Revolutionary War it was reported that there were only six guards at Old Point Comfort. The War of 1812 further exhibited the need of an adequate coastal defense system when British troops marched on Washington and set fire to our nation's capitol.
In 1816 a board was appointed by acting Secretary of War George Graham to make recommendations for a coastal defense system for the United States. Brevet Brig. Gen. Simon Bernard, a former aide-de-camp to Napoleon, headed the board, which planned a series of forts to extend from Maine to Louisiana. Bernard is reputed to have personally designed Fort Monroe. Collection of materials for the fortifications at Old Point Comfort was begun in 1818, and actual construction began in March 1819. At this time, construction had also begun on Fort Calhoun, which was to be built on an artificial island in the middle of Hampton Roads.
Fort Monroe was designed following the general plans of the fortifications designed by Marshall Vauban at Toul, France. It consisted of seven fronts and covered approximately 63 acres of ground. The original armament was planned to be 380 guns, later extended to 412 guns, but they were never all mounted. The fort housed a peacetime garrison of 600 men and a planned wartime garrison of 2,625 men. No other fort in the United States was of comparable size, and no fort in Europe not enclosing a town was any larger.
Fort Monroe received its first official U.S. Army garrison on July 25, 1823, when Company G, Third United States Artillery, was transferred from Fort Nelson, near Norfolk, to guard military convicts being used in the construction programs. In 1825, Fort Monroe's garrison was the largest in the United States, with one-third of the artillery troops and approximately one-tenth of the entire U.S.Army within its walls.