Irregulars

How Francis Hoyt Gregory’s Remarkable Career Spanned Three Wars

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.

Francis Gregory

Francis Gregory

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.

Gregory also 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 2022.

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