Norwalk native Francis Hoyt Gregory (1789-1866) is one of few Americans to play a role in the War of 1812, the Mexican-American War and the Civil War.
First, he survived capture by the British before and during the War of 1812. He was actually imprisoned twice, first as a merchant mariner and then as a naval officer.
He was the third great grandson of John Gregory, the founding settler of Norwalk, Conn. Gregory left Norwalk for the sea at an early age; he was still a teenager when the British press-ganged him to serve on one of their ships. He escaped, and President Thomas Jefferson in 1809 appointed him a midshipman aboard Oliver Hazard Perry’s Revenge. He later saw action in the War of 1812 on Lake Ontario, where the British captured him and held him until 1815.
Francis Hoyt Gregory, Guerilla
Before his capture, however, Gregory as acting lieutenant undertook a series of daring raids in Canadian waters. In June of 1814, he and his men took three small boats to Tar Island in the St. Lawrence River. They hid until they spotted a British gunboat, the Black Snake, patrolling the Thousand Islands. The Americans set out in their boats and approached the Black Snake, waving and smiling. The British, thinking them friendly, held fire. Gregory led his men onto the Black Snake, where they captured all 20 British and Canadian sailors.
Soon, however, two British gunboats spotted the Black Snake. Realizing the likelihood of capture, Gregory ordered everyone into the three small boats and sank the Black Snake. The British, distracted, left them alone to return to American lines.
Less than a month later, Gregory and his raiders sneaked into a Canadian shipyard and set fire to a British schooner just two weeks away from launch. Not only did they destroy the vessel, but a storehouse as well.
Then in late August, the British captured Gregory on Lake Ontario after he and his raiders burned a raft carrying timber to a shipyard. He spent the rest of the war in an English prison.
But Gregory did his share of capturing prisoners during his 50-year naval career. As a young gunboat captain, he helped capture three Spanish pirate ships in the Gulf of Mexico and an English brig smuggling slaves into New Orleans. Later he captured or destroyed pirate ships in the Caribbean. During his career he fought pirates off the Barbary Coast, blockaded the Mexican coast during the Mexican-American War, sailed a frigate to Greece to support the revolutionary government and commanded the Boston Navy Yard.
Finally, during the Civil War, Gregory, then in his 70s, came out of retirement to supervise the construction of ironclad gunboats. He won promotion to rear admiral and died soon after the war. He is buried in New Haven.
Francis Hoyt Gregory, POW
His family tells a terrific story about his early imprisonment by the British that illustrates his determined spirit. His captors took him to England and held him on a country estate. They allowed him his freedom within certain boundaries under a gentleman’s agreement not to escape. A stone marked one of those boundaries.
Gregory decided to attend a dinner party at a neighboring estate. When he arrived, he was accused of violating his agreement to stay within boundaries. He brought the guests outside, however, and pointed to a wheelbarrow. It held the stone marker that he brought with him to expand his range.
This story about Francis Hoyt Gregory was updated in 2023. With thanks to Small Boats and Daring Men: Maritime Raiding, Irregular Warfare, and the Early American Navy” by Benjamin Armstrong.