1714 - Thomas Williamson (?-1742) possesses 15,000 acres in Henrico
1731 - Captain John Williamson (?-1757) builds Brook Hill farmhouse
1764 - Robert Williamson II (1764-1796) is born at Brook Hill
1796 - Robert Carter Williamson (1796-1863) born at Brook Hill

1818 - Robert C Williamson marries Lucy Parke Chamberlayne
1822 - She dies after giving birth to daughter Mary Amanda Williamson
1830s - John Stewart arrives in America
1842 - John Stewart buys Brook Hill from his future father-in-law
1843 - John Stewart marries Mary Amanda Williamson
1844 - Mary Amanda Stewart born at Brook Hill. John Stewart hires noted architect Robert Mills to design an addition to house his growing family
1847 - Belle Stewart born at Brook Hill
1849 - Marion McIntosh Stewart born at Brook Hill
1851 - Lucy Williamson Stewart born at Brook Hill
1853 - Annie Carter Stewart born at Brook Hill
1860 - John and Daniel Stewart donate land and money for the creation of Emmanuel Episcopal Church
1861 - War! Brook Hill serves as a camp and hospital, receiving numerous Confederate officers as visitors
1862 - Elizabeth Hope Stewart born at Brook Hill
1864 - Battle of Yellow Tavern, just two miles north of the house
1870 - Mary Amanda Stewart weds Capt Thomas Pinckney at Brook Hill
1871 - Belle Stewart marries Joseph Bryan. They live at Brook Hill until the 1880s, when they move to Laburnum. John Stewart Bryan born at Brook Hill
1873 - Robert Coalter Bryan born at Brook Hill. Robert Carter Williamson dies
1874 - Jonathan Bryan born at Brook Hill
1875 - Charles Cotesworth Pinckney, the only Pinckney child of five to live to adulthood, is born at Brook Hill
1879 - Joseph St. George Bryan born at Brook Hill
1882 - Thomas Pinckney Bryan born at Brook Hill
1884 - Marion McIntosh Stewart marries Rev George Peterkin
1885 - John Stewart the patriarch dies, leaving his wife and four maiden daughters to manage Brook Hill
1889 - Mary Stewart Pinckney dies, and her surviving son Charles Cotesworth is sent to live at Brook Hill. John Stewart's brother Daniel dies, leaving his fortune to the Brook Hill family
1890 - Mary, the only surviving child of the Peterkins is born

1910 - Mary Williamson Stewart, the matriarch, dies age 88
1936 - Hope Stewart dies
1938 - Norma Stewart dies
1947 - Lucy Williamson Stewart dies
1957 - Annie Carter Stewart dies, aged 104. Her will provides for the upkeep of Brook Hill and defines the lines of descent for caretakers
1959 - Joseph Bryan III becomes the caretaker of Brook Hill
1992 - The top floor of the back wing is removed and the roof lowered
1993 - Joseph Bryan III dies, and his daughter Joan B Gates becomes the caretaker of Brook Hill