Carskadon was a Scotch-Irish immigrant and served several terms in the Virginia State legislature. He also served as Just of the Peace after being elected in 1837. During his time as a member of Virginia's General Assembly, Carskadon spoke out against the violence of slavery, despite being a slave owner himself. As a gesture to his commitment to the abolitionist cause, he freed his slaves before his death in 1855.
Carskadon's son, Thomas R. Carskadon was born on the property in 1837. The younger Carskadon would go on to be a political figure as a Whig party member and later a Republican. When Carskadon became a Republican party member in 1860, he became so intensely unpopular among his neighbors that his home and other properties were often vandalized. Carskadon even received threatening letters. Two years after this decision, Carskadon became an advocate for West Virginia Statehood and traveled to Wheeling to draft plans for the new local government. Presidents Lincoln and Johnson both gave him appointments in assessor roles for the newly formed state. As Carskadon became more and more radical, he was removed from his position.
Despite losing his position as an assessor, Carskadon was successful within the Republican Party and was elected to multiple high-ranking positions within the party. Later in his life, Carskadon became a strong advocate for Prohibition. He was such a prominent figure among prohibitionists that he was nearly put forward as a presidential candidate and briefly ran as a vice-presidential candidate in 1896. Just ten years after this unsuccessful bid for office Carskadon died on this property. His descendants continued to be involved political leaders, rising to several prominent state offices.