Bolling was born about 1737, probably on the Amelia County estate of her parents, Thomas Tabb and Rebecca Booker Tabb. Her father was one of Virginia’s wealthiest merchants, and her standing was further secured on April 11, 1758, when she married Robert Bolling, of Dinwiddie County, scion of another wealthy merchant family. They had two sons and four daughters.
Bolling inherited £10,000 from her father in 1769. Following her husband’s death on February 24, 1775, she assumed the management of an enormous estate. The property, much of it in Amelia County, included plantations and scores of enslaved people. Bolling also managed warehouses, a gristmill, and much of the land on which the rapidly growing town of Petersburg was built. By 1790 she owned thirty-three of the town’s most valuable lots, four of its eight tobacco warehouses, and at least thirty-eight enslaved people who lived in the town. Bolling paid taxes on more than 10 percent of Petersburg’s total taxable wealth.
During the American Revolution, Bolling earned a reputation for exceptional mettle. Many residents fled when the British army occupied Petersburg briefly in the spring of 1781. Bolling stood her ground, hoping to save her property from destruction. British officers placed her under house arrest and established their headquarters at Bollingbrook, her residence and the largest house in town. Before they left, the British confiscated her horses and burned her tobacco. Bolling persuaded them to return her enslaved laborers, however, and the British spared her warehouses and mill. After a visit to Bollingbrook the following year, the Marquis de“lively, active, and intelligent; [she] knows perfectly well how to manage her immense fortune, and what is yet more rare, knows how to make good use of it.” This combination of character and wealth likely would have won a man high public office, military honors, or distinction in one of the learned professions—perhaps all three. But however great their talents, women were excluded from all such positions of public authority.
Because she never remarried, Bolling could take advantage of a legal system that authorized single women and widows to exercise control over property. In the thirty-nine years of her widowhood she engaged in almost every kind of transaction. Bolling served as an executrix and a guardian. She bought and sold land, rented out houses and shops, and took debtors to court. Like other cautious mothers, Bolling settled a separate estate on one daughter to prevent any risk of the property being seized by the creditors of her son-in-law. Other transactions reflected the institutional development of Virginia towns in the early republic. Bolling invested heavily in two new banks, petitioned the assembly to empower Petersburg to pave its streets, and in 1787 gave land to the town for its municipal offices. She contributed to a fire company, a theater company, the Episcopal Church, and the Female Orphan Asylum.
A tough-minded proprietor, Bolling, unlike some of her female contemporaries in Petersburg, evidently freed none of her enslaved people. When she wrotenot long before her death, she distributed her wealth, including the enslaved individuals, according to her notions of the varying deserts of her heirs, rewarding some and slighting others. This personalized style of bequest became commonplace among Petersburg women later in the century, but Bolling was unusual in stipulating that heirs who contested her will would be cut off. On or shortly before October 28, 1814, Bolling died, probably at Bollingbrook. She was buried in the family graveyard.