Orlando Brown, the second child of John Brown and Margaretta Mason Brown, was born September 26, 1801 in Frankfort. He arrived only a few months after John, Margaretta, and eldest son Mason moved into Liberty Hall. As a child, Orlando was probably educated at home by their mother or by private tutors, but as a teenager, Orlando went to Danville, KY, to study with renowned educator Kean O’Hara in preparation for college. Like his father, Orlando attended Princeton University in New Jersey and graduated with an A.B. in 1820. After Princeton, Orlando attended Transylvania University in Lexington, KY, and graduated with a degree in civil law in 1823.
Orlando seems to have been popular with both his friends and female society, although he only had eyes for his first cousin, Mary Watts Brown, who was seven years his junior. They began a cat and mouse game when he was eighteen and she was only 12! When Mary announced to Orlando that she “did not and could not love him” in 1824, Orlando moved south to Tuscumbia, Alabama in an effort to forget about her, and practiced law there for several years. He moved back to Frankfort in 1929 when his law partner died. Orlando and Mary Watts were finally married July 29, 1830 and had five children together: Euphemia Helen (1831-1891), John Mason (1834-1835), Mason Preston (1836-1874), Orlando Jr. (1838-1891) and a stillbirth in 1840.
In order for Orlando to have the same inheritance as his older brother Mason, Senator Brown built a home for Orlando and Mary in 1835, next to Liberty Hall. The house, designed by Gideon Shryock, was completed at a total cost of $5,000. In 1841, Mary’s health began to decline and she passed away in August of that year. All reports say that Orlando was absolutely devastated by Mary's death.
Although trained as a lawyer, Orlando’s true passion seemed to be writing. In 1833, Orlando became the editor and joint proprietor of The Frankfort Commonwealth, a newspaper with a Whig bias. Washington Irving, author of The Legend of Sleepy Hollow, told Orlando that he shouldn’t be wasting his talent on newspapers, but should be writing books of literary merit “to delight and educate his age.” In 1836, Orlando joined his father in the creation and organization of the Kentucky Historical Society and acted as the Society’s first corresponding secretary. In 1848 Orlando served as Kentucky’s Secretary of State under Governor John J. Crittenden, but resigned the post in 1849 to accept a position in President Zachary Taylor’s cabinet as Commissioner of Indian Affairs. The job did not suit Orlando, and his reputation was badly tarnished when his superiors used him as a scapegoat. Orlando quickly resigned in 1850 and went home to Frankfort.
Orlando married Mary Cordelia Brodhead, the widow of his close friend Lucas Brodhead, on October 12, 1852. Cordelia and Orlando had no children together, but they raised her six children and his three living children as a family. During the Civil War, Orlando served as a recruitment officer and was awarded the rank of Colonel. He has the distinction of being the first honorary Kentucky Colonel, serving as a symbolic guard for state events and social functions. Orlando partnered with Mason on several ventures around Frankfort – together they helped create the Frankfort Cemetery and owned a theater.
Orlando died on July 26, 1867, probably from tuberculosis, and is buried in the Frankfort Cemetery. There are no living descendants representing Orlando’s branch of the Brown family.