Before its European exploration, the area around Midway was inhabited by the Mound Builders.[which?] Two large and several smaller American Indian mounds have been identified on nearby farms.
The present city began as a small settlement known as Stevenson's at the time of its first post office in 1832. On January 31, 1835, the local farmer John Francisco sold his 216.375-acre (87.564 ha) farm to the Lexington and Ohio Railroad for $6,491.25. The railroad then used the land to establish Kentucky's first railroad town, naming it Middleway for its location relative to Lexington and Frankfort, Kentucky. (The town is also equidistant between Versailles and Georgetown.) The major streets of Midway were named in honor of the railroad's original officials. It was renamed Midway in 1837.
Distilling Bourbon in Midway – Midway has a very rich history of distilling Bourbon for nearly a 100 year period from 1865 to 1959. The Distillery was located at the corner of Gratz Street and Dudley Street, nestled in the bend of the Lee's Branch of the North Elkhorn Creek. There were several owners over the years, with the Distillery operating under various business names. Buford, Guthrie & Co. 1865-67, A. Buford Distillery 1867-68, Keller Distillery 1868-77, 1878-89, S.J. Greenbaum Distillery 1890-1911, Belle of Anderson Distillery 1912-14, Midway Distilling Co. 1915-24, Destroyed by fire in 1924 and closed from then till 1933, rebuilt and operated as the Woodford County Distilling Company 1933-40, Park & Tilford Distillery 1941-53, Schenley Products Distillery 1954-59. Early in the 1960s, Schenley Products donated the property, building, and equipment to the Midway Woman's College. Notable national brand names produced include Belle of Bourbon, Belle of Lexington, Belle of Anderson, Glenarme, Arlington, Jessamine, and Woodford. Two buildings still remain, currently known as The Robin's Nest, previously a distilling building and The Midway Loft Apartments, previously an aging warehouse. A large Distillery warehouse fire occurred on August 4th, 1908, where over 47,000 barrels of bourbon were destroyed. The Lee's Branch was on fire for over one mile, and several Midway residents were scorched dipping tin cups into the Lee’s Branch for Bourbon and Water. Martin Street next to the Lee’s Branch was nicknamed “Tin Cup Alley”. The Midway Fire Department was recognized for saving the City and the Female Orphan's School.
In 1920, during a robbery of the distillery, Benjamin Rodgers and Homer Nave was killed. Richard W. James was arrested for the killings. He admitted to the robbery but denied shooting the men, and claimed that the facility's superintendent of bottling, Samuel Seay, had a deal with James and others to share the proceeds of the stolen liquor. James was convicted of murder, but one member of the jury refused to vote for his execution on religious grounds. On March 13, 1921, a mob took James from the county jail in Versailles, Kentucky, and lynched him from a tree near Margaret College, about a half-mile from Versailles. No one from the mob was indicted and, when Gov. Edwin P. Morrow removed the sheriff from his post, local voters elected his wife to replace him.
Midway Historic District comprises much of downtown Midway and is listed on the National Register of Historic Places.
Midway is located in the northern section of Woodford County in the Bluegrass region of Kentucky, an area with farms that produce tobacco, corn, soybeans, cattle, and horses. Midway is located at 38°9′2″N 84°40′59″W (38.150484, -84.683014). According to the United States Census Bureau, the city has a total area of 1.1 square miles (2.8 km2), all land.
As of the census of 2000, there were 1,620 people, 623 households, and 409 families residing in the city. The population density was 1,484.3 per square mile (573.1/km2). There were 672 housing units at an average density of 615.7 per square mile (237.7/km2). The racial makeup of the city was 89.81% White, 7.72% African American, 0.31% Asian, 0.06% Pacific Islander, 1.17% from other races, and 0.93% from two or more races. Hispanic or Latino of any race were 1.42% of the population.
There were 623 households out of which 28.6% had children under the age of 18 living with them, 54.1% were married couples living together, 8.8% had a female householder with no husband present, and 34.2% were non-families. 28.9% of all households were made up of individuals and 11.7% had someone living alone who was 65 years of age or older. The average household size was 2.38 and the average family size was 2.96.
21.0% of the population was under the age of 18, 14.1% from 18 to 24, 29.9% from 25 to 44, 21.6% from 45 to 64, and 13.3% who were 65 years of age or older. The median age was 35 years. For every 100 females, there were 75.3 males. For every 100 females age 18 and over, there were 73.0 males.
The median income for a household in the city was $50,909, and the median income for a family was $60,326. Males had a median income of $35,795 versus $32,500 for females. The per capita income for the city was $24,528. About 2.0% of families and 3.6% of the population were below the poverty line, including 0.6% of those under age 18 and 14.2% of those age 65 or over.