Anna Mary was the first child born here at Riddick's Folly on July 21,1841. She was the oldest child of Nathaniel and Missouri Ann Jones Kilby Riddick. Her father Nathaniel was a lawyer later a judge and was also a member of the Virginia Legislature. Her mother Missouri attended St. Joseph's Academy in Emmitsburg, Maryland from 1835-1837. Anna Mary's siblings were Mills Edward, John Thompson, Missouri Taylor and twins Nathaniel Henley and Cordelia Kilby. Unfortunately, Cordelia Kilby died at birth.
As a young lady Anna Mary attended Hayden Hall in Smithfield. She also attended Norfolk Female Institute where she met Jonathan Reynolds Smith and Ellen Alice Smith. She was well read, loved to sew and paint and was an accomplished pianist. Ellen and Anna became very close friends and kept in constant touch through out their lives. After being a teacher at the Norfolk Female Institute Jonathan became a tutor for Anna Mary's brothers. Jonathan ( affectionately known as Jonnie to Anna) joined the war effort in 1861. While stationed on Craney Island he witnessed the battle between the Monitor and the C.S.S. Virginia ( formerly known as the Merrimac). Jonnie was later killed at Malvern Hill in 1862. Anna and her family fled to Petersburg during the Union occupation. At that time Major General John J. Peck had taken occupancy of their home and made it his headquarters. Union soldiers occupied the home from 1862-1865.
After the war Anna Mary and her sister Missouri (Zouzie) were determined to restore Suffolk to its former glory and to help those families affected by the War Between the States. Together they started the Mite or Ladies Aid Society; they also founded the Randolph Society of St. Paul's Episcopal Church. She was a charter member and president of the Suffolk Chapter of the Daughters of the Confederacy for 30 years and a charter member of the Association for the Preservation of Virginia Antiquities, King's Daughters, Daughters of the American Revolution, and even a member of the Suffolk Literacy Club. Anna Mary was the first women to vote in Suffolk. She lived in Riddick's Folly until her death on November 11, 1936 and never married.