- Main article: Emma Simpson
Emma Simpson (September 17, 1849 – 1917) was the daughter Robert and Mrs. Simpson. Her father and elder brother fought in Civil War for the Confederate States Army. She lived in Gordonsville, Virginia, where she was home-schooled by her mother. In 1864, her aunt Caroline and cousin Rachel came to live with at her home, after her mother fell ill. Later that year, Emma's home was occupied by Union forces for several months.
Caroline ColstenCaroline Colsten (died 1893) was the mother of Rachel and Elizabeth. She was close to Mrs. Simpson, whom she resembled "in appearance and manner." In February 1864, she moved to Gordonsville to take care of the ailing Mrs. Simpson. Caroline continued to live at the Simpsons' home to help Emma manage the household. After the war, Caroline turned the Simpsons' house into an orphanage, known as "Aunt Caroline's Home." The orphanage closed, when she died at the age of sixty-two.
IrisIris was one of the Simpsons' slaves. She helped Mrs. Simpson with the household chores. Her daughter, Dinah was Mrs. Simpson's most fervent students. Iris had nursed Emma as a baby and remained loyal to her. In 1864, Iris, unlike the other slaves, stayed at the Simpson house, which perplexed the Union soldiers. After Emma's marriage, Iris and her daughter moved with the newlyweds to Richmond. By 1875, Iris married and moved north, possibly to Chicago.
Rachel ColstenRachel (c. 1846 – 1868) was Emma's older cousin. She lived with her parents, Caroline and Benjamin, in Richmond and attended an all-girls school, until the Civil War. At school, she shared a dormitory with four girls and was best friends with her roommate, Susan Anne Taylor. She was talkative, strong-willed, and opinionated. Rachel suffered from what appeared to be a nervous breakdown during the war. She was committed in 1867 to lunatic asylum, where she died a year later.
Mrs. SimpsonMrs. Simpson (died April 18, 1864) was the mother of Emma and Cole. Her husband and son fought in the Civil War for the Confederates. In her husband's absence, Mrs. Simpson took care of the whole household with the help of several "reliable" slaves, including Iris, Amos, and Nelson. She was in charge of Emma's education, and also taught the youngest slaves. In January 1864, Mrs. Simpson fell ill and never recovered, finally succumbing to death four months later.
Tally MillsTaliaferro "Tally" Mills (c. 1846 – 1916) was a soldier that fought during the Civil War. His parents died in a house fire around 1861, while he was away at school. In July 1863, he met Emma at a party in Richmond. Shortly later, he wrote to her telling her he had joined the Confederate army. He continued writing to Emma frequently. Tally was held prisoner by the Union Army, until May 1865. Later, he married Emma and they moved to Richmond, where they raised their two children, Robert and Jane. Tally became a journalist for The Richmond Examiner and later started his own small newspaper.
- Amos Braxton (died 1896) was the Simpsons' loyal and reliable slave. He stayed with the family throughout and after the Civil War. Amos, an accomplished carpenter, fixed up the Simpson home, which became an orphanage. He continued to live there until his death.
- Benjamin Colsten (died July 1863) was the husband of Caroline, and the father of Rachel and Elizabeth. He died fighting in the Civil War. Benjamin was good friends with Mr. Simpson.
- Mrs. Broyles was the Simpsons' neighbor in Gordonsville. Her husband died in 1863, while fighting in Gettysburg. She was the mother of Robert, Tom, Lily, and Lucy. After the Union soldiers invaded her home, she and her daughters moved into the Simpson residence.
- Cinda (died July 23, 1864), a child slave of the Simpsons'. She became ill with scarlet fever.
- Cole Simpson (died 1863) was Emma's elder brother. He fought on the Confederate side during the Civil War. He died of pneumonia, while recovering from injuries sustained in Richmond.
- Colonel Davenport, a Union officer. His troop temporarily took over the Simpsons' house and he set up his office in the library. Later, him and his suddenly soldiers moved out without warning.
- Denise and Dolphy, two of the Simpsons' slaves. Dolphy was their seamstress and Denise worked as a cook.
- Dinah was Iris's daughter. She always showed up on time for Mrs. Simpson's school. After Mrs. Simpson's death, Dinah attended lessons with Emma. She enjoyed learning how to write and spell. After the war, she and her mother moved to Richmond, where they worked for Emma.
- Elizabeth Colsten (July 12, 1863 – December 21, 1864) was the daughter of Caroline and Benjamin.
- Mrs. Fellers was the widow of Jack Fellers, who died sometime in 1864. Emma and presumably Caroline visited to give her the news of her husband's passing. They were married for less than a year.
- Mr. Garlington (died October 1864), the Simpsons' neighbors. He was supported the Confederates, believing they would "emerge victorious." Later, he was found murdered, presumably by his own slave.
- Mrs. Garlington was Mrs. Garlington's soft-spoken wife. She was horrified by her husband's murder.
- Doctor Harris was the local Gordonsville physician. In early 1864, he treated Mrs. Simpson, but was unable to make her well.
- Lily and Lucy Broyles were Mrs Broyles' daughters. Their father died in the Civil War. In 1864, their brothers returned home due to severe injuries. They later moved into the Simpsons' home.
- Martha is a distant cousin of Emma. She and daughter, Bettie, visited the Simpsons' home in 1864, after recovering from the measles.
- Nelson was described as one of the Simpsons' reliable slaves. He was in charge of the family's crops, horses and livestock. In late 1864, he ran away with a lot of the other slaves.
- Captain (died 1864) and Mrs. Rawlings were neighbors to the Simpsons'. He fought in the Civil War and drowned, before he could return home. Their baby daughter died in February 1864.
- Robert and Tom Broyles (died July 28, 1864) were Mrs. Broyles' sons. They were injured in battle and sent home to recuperate. Robert disappeared soon after his brother's death.
- Colonel Robert Stiles Simpson (died October 19, 1864) was Emma's father, whom she corresponded with through letters. He remained positive about a Confederate victory. Robert was mistaken for a Union soldier and was shot during the Battle of Cedar Creek. He was buried next to his wife.
- Romeo was Mr. Garlington's slave. Around 1861, Mr. Garlington sold his wife and child off. He was believed to have been behind the plot that killed Mr. Garlington.
- Sally Robbins (born c. 1846) was the fiancee of Lieutenant Charles Jones. She visited the Simpson residence and received a lecture from Rachel about marriage.
- Susan Anne Taylor was Rachel's best friend and roommate. She attended an all-girls school, until it closed due to the war.
- Emma Clark Broughton was Emma's great-great-granddaughter. She inherited Emma's ring, which Tally had given her in 1864. Emma worked as a journalist in New York City.
- Jane (born 1869) and Robert Mills (born 1868) were the children of Emma and Tally. Emma named her daughter after the title character in Jane Eyre.