Midway is a city in Woodford County, Kentucky, United States. Its population was 1,620 at the 2000 census. It is located midway between Frankfort and Lexington along the single-track railroad between them. It is part of the Lexington-Fayette Metropolitan Statistical Area. The town is home to a major thoroughbred race horse breeding operation, Three Chimneys Farm. In 2003, faced with a declining downtown, a major streetscape renovation project began as part of Main Street Kentucky. New period structures and lighting brought new life to the town.
The area around Midway was inhabited by Indian Mound Builders. Two large Indian mounds have been identified on nearby farms, as well as several smaller mounds.
What is now the town of Midway, was once a farm belonging to John Francisco "consisting of two hundred and sixteen acres, one rood and twenty poles of land". It was sold to the Lexington and Ohio Railroad Company on 31 January 1835 for $6,491.25. It became Kentucky's first railroad town. Midway was purposely located an equal distance between the cities of Lexington and Frankfort, along the railroad. The town is also equidistant between Versailles and Georgetown. The major streets of Midway were named in honor of the railroads first officials. Midway shows up as Leesburg on two 1850s era Kentucky maps