Simon Dewitt was born in 1822 in New York State. The Civil War broke out when he was 39 years old and, when African American enlistments were authorized in 1863, he enlisted at age 41, joining the 29th Connecticut Infantry Regiment. The 29th Connecticut Infantry Regiment was a notable regiment, credited with being one the first to enter Richmond, Virginia after the city had surrendered to Union forces. Dewitt served as a private during this war, and was never promoted. His physical characteristics were well recorded and very detailed. He was described as having black hair, black eyes, and his skin complexion was “colored”. Simon was also listed as being 5 foot 4 ½ inches tall. This was below the average height of American males during the Civil War, which was around 5 foot 7 inches tall. In the course of his service, DeWitt was disabled on October 24, 1864 and was later discharged about a year later on October 24, 1865. Twelve years after Dewitt was discharged from the war he married Mary Jane Warner on October 14th, 1877. At the time of their marriage, Simon was 55 and Mary was 47. They lived in Canaan, Connecticut and had no children. In their official marriage certificate both Mary and Simon were labeled as colored. Shortly after their marriage Simon decided to appeal for his pension on October 31, 1887. He would eventually receive his pension for the disability that he sustained in the war. In his pension record his disability was listed as being caused by a rupture in his right groin, along with fever and chills, and a back injury that occurred during war. Almost a decade letter Dewitt stopped receiving payment from his pension after he was reported dead from spinal paralysis on June 13, 1898. After his death and loss of pension payments, his wife Mary applied for a widow's pension and eventually received it.