 In the summer of 1863, he recruited and helped lead the First North Carolina Colored Volunteers, which became part of the 35th United States Colored Troops.After being wounded in the Battle of Olustee, Florida, in February 1864, he was assigned to garrison duty in South Carolina, which was occupied by Union troops.Following the war and his honorable discharge in 1866, Singleton moved to Connecticut, where he worked and taught himself to read and write.