Designed by Brigadier General of Engineers Simon Bernard, an expatriate Frenchman who had served as a general of engineers under Napoleon, Fort Wool was constructed on a shoal of ballast stones dumped as sailing ships entered Hampton's harbor and was originally intended to have three tiers of casemates and a barbette tier with 216 muzzle-loading cannon, although it never reached this size.

[8] In 1902, as a result of the Endicott Board's findings,[9] all of the original fort, except for eight casemates at the west end, was demolished and new fortifications were constructed.

[10] Only the six original three-inch guns remained in 1942, when two were sent to nearby Fort John Custis on Fisherman Island.

[11] Brigadier-General of Engineers Simon Bernard was tasked by Secretary of War John C. Calhoun to create or improve fortifications for the protection of vital U.S.

With four tiers, it was planned as the first "tower fort" of the third system, resembling the four-tier Castle Williams in New York harbor.

It was to be built on a 15 acres (6.1 ha) artificial island southeast of Old Point Comfort in Hampton, Virginia.

[14][15] Construction of the fort began in 1826, and after considerable delays caused by subsidence of the island, two-thirds of the first level of casemates was finally completed in 1830.

He found that the island would not hold the weight of the two tiers of casemates and brought more stone in to stabilize it, but the fort never reached its intended size.

[15] The fort was originally named after John C. Calhoun, President Monroe's secretary of war who was a Southern politician of secessionist tendencies.

[15] A long-range experimental cannon, the Sawyer gun, was installed at Fort Calhoun in mid-1861 during the Civil War.

[18][19] The range of this weapon extended all the way to Sewell's Point, more than three miles away (where the Norfolk Naval Base is now located),[4] the site of a Confederate earthen fort with bastions and a redan and three artillery batteries totaling 45 guns.

The fort can also be seen by westbound vehicles on approach to the HRBT southern tunnel, which carries Interstate 64 across the mouth of Hampton Roads.

[25] The island, now called Rip Raps, continues to settle, and occasionally the casemates of the original fortress are off-limits for safety reasons.

This took place during a parade of tall ships sailing past the fort, part of the 400th anniversary celebrations of the settlement of Jamestown.