The Original Highlands neighborhood was built on land surveyed in 1774 and granted to Colonel William Preston. His son, Major William Preston, and wife moved onto the land in 1814 and established a plantation called the “Briar Patch”.
The 1819 construction of the Louisville and Bardstown Turnpike, now Bardstown Rd, would eventually lead to many people moving to the area. The addition of horse drawn street cars would spur a development boom that eventually led to the additional neighborhoods to include the Original Highlands, Cherokee Triangle, Phoenix Hill, Irish Hill, Tyler Park, Deer Park, Bonnycastle, Highlands-Douglass, and Belknap. These neighborhoods are collectively known as The Highlands. .