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Winchester was named after Winchester in Virginia. The city was founded in 1793 on a land area of 66 acres. The land was donated by John Baker—a frontiersman. In 1812, the city was the seventh largest town in Kentucky.
The population of Winchester is about 18,413 people. The city features the Bluegrass Heritage Museum with many original exhibits with attributions to local lore. The city hosts a year-round exhibit dedicated to Homer Ledford—a renowned instrument maker and bluegrass musician from Kentucky. His dulcimers, banjos, mandolins, guitars, and ukuleles are sought by musicians all over the world. The city also has a civil war fort at Boonesboro commemorating Union soldiers. The fort was built to defend the ford and ferry at Boonesboro. Very little of it remains today.
The city is known for being a place for "original and local experiences", ranging from hand-on history to Ale-8 and much more. It is located just outside of Lexington.