The neighborhood was built on land surveyed in 1774 and granted to Colonial William Preston, surveyor of Fincastle County, Virginia.

He died in 1781, and eventually his son, Major William Preston, and wife moved onto the land in 1814 and established a plantation called the "Briar Patch".

[2] The area was simply called the Highlands because it sits on a ridge between the middle and south forks of Beargrass Creek, above the Ohio River flood plain.

In recent years the area has attracted many professionals because of its proximity to downtown and the Baxter Avenue/Bardstown Road and Barret Avenue commercial corridors which include arts galleries, eclectic shopping, and night life.

The Barret Avenue commercial corridor is an emerging art zone due to the large number of galleries.

Held on Baxter Avenue each September, the festival features local and national music acts along with art and vendor booths.