The area eventually known as St. Matthews was first settled in 1779 by Col. James John Floyd. Floyd, who had conducted an important survey of Jefferson County in 1774, bought 2,000 acres (8 km²) of land from veterans who had been awarded the parcels for their service in the French and Indian War. He arrived overland on November 8, 1779, bringing several family members and a black slave. They built cabins and a stockade, which came to be known as Floyd's Station.^[3]

During the early 19th century, the area held several plantations and was known as the "garden of the state". As with most areas of the Inner Bluegrass Region, farm labor was generally provided by African slaves. The major crops were tobacco and hemp; breeding livestock, primarily horses, was also important to the economy.^[4] In the years before the Civil War, Kentucky planters were generally selling their slaves at markets in Louisville to be sent to the Deep South, where the European demand for sugar and cotton made their use more profitable.

The community developed around the intersection of present-day Breckenridge Lane, Shelbyville Road, and Westport Road. By 1840, it was known as Gilman's Point, after local tavern owner Daniel Gilman. The name "St. Matthews" emerged in 1850 after the completion of St. Matthew's Episcopal Church, the area's first. It became the official in 1851 when the newly opened post office adopted it. Numerous other Protestant churches were soon founded, and Holy Trinity, the oldest of the three Catholic churches in the city was completed in 1882).^[5]Trinity High School was established nearby in association with the church... (read more)