Her father was writer and judge Nathaniel Beverley Tucker, a prominent advocate for States Rights, southern unity, and the continuation of slavery.

The couple's marriage took place early in the American Civil War, and soon Charles joined the Confederate army to work as a surgeon while she remained in Williamsburg.

During the 1862 Peninsula campaign, Williamsburg was occupied by the Union army, and, by 1863, Cynthia had moved to North Carolina, only returning after the war ended.

To raise money, the association gathered ivy and early flowers for sale, sold baked goods, and collected donations.

[1] Inspired by this success (and after an altercation with the rector of Burton church over funds), she redirected her efforts to preserving other historic buildings in Williamsburg, many of which were in a state of dilapidation.