The dream of John Leak, who had settled in Rockingham County, North Carolina north of the Dan River on Matrimony Creek around 1773 and amassed great landholdings such that he decided to establish Leaksville in 1795. Leak selected a high bluff near the confluence of the Dan and Smith rivers and laid out the town in half-acre lots along the town's original streets - Water, Patrick, Henry, Hamilton, Washington, and Jay. Thomas Searcy made the first recorded purchase of a town lot that same year.

In anticipation of a tobacco trade, John Leak and Robert Coleman were appointed tobacco inspectors in 1796. In 1797, the General Assembly chartered the town - with Leak, Coleman, Alexander Sneed, Nathaniel Seals, and Terry Hughes as the first town commissioners. In 1800, the General Assembly approved the establishment of two taverns.

According to Alexander Sneed's 1810 description, Leaksville was "a most delightful Spot, and the best situated for trade, perhaps, of any in the County, as it commands a very extensive back Country, the produce of which would inevitably center here." However, the small town grew slowly and by 1800 John Leak had lost much of his property via poor management.

According to US Post Office records, the town was spelled Leakesville when it obtained its Post Office on February 3, 1817, and its first Postmaster was John Lenox. Soon thereafter the second "e" was dropped, even in Post Office Department records, and the town retained its unique Post Office until August 22, 1924, when a combined PO named Leaksville-Spray was chartered - it was closed down on December 31, 1926. Spray is another town very nearby that had been established in 1890.

The town of Leaksville was merged with Spray and Draper in 1967 and no longer exists as a single entity. Click Here for a website dedicated to the preservation of the Leaksville history.