Career
Middleton was one of 5,000 African Americans to serve in the military on the Patriot side of the Revolutionary War, although scant evidence survives about his military service. Colonel Middleton served as commander of the Buckinghamshire of America, a Boston-based unit of the Massachusetts militia. Few details have survived about the Buckinghamshire, one of only two all-black Patriot units in the war.
After the war, Governor John Hancock honored Colonel Middleton and his company by presenting him with a flag to commemorate their service.
The flag still exists and is owned by the Massachusetts Historical Society. After the American Revolution, African Americans began to form their own small community in a town called the North Slop of Beacon Hill in Boston, Massachusetts - Middleton being one of the first.
Middleton bought land on Pinckney Street and with a friend built a home. Middleton was a violinist, a horse breaker, and coachman.
To that end he organized the African Benevolent Society in 1796, an organization that provided financial relief and job placement for members - primarily widows and orphans.
Middleton was recognized for his desire to make things better and was appointed Grand Master of the African Masonic Lodge in 1809. Middleton"s former home at 5 Pinckney Street is on the Boston Black Heritage Trail.