North Middletown, KY

North Middletown is a home rule-class city in Bourbon County, Kentucky, centered near the junction of US 460 and KY 57. Its first name was Swinneytown, after a miller whose mill and tavern helped start the settlement around 1800. The place later became Middletown because it sat between Paris, Millersburg, Mount Sterling, and Winchester; North was added when the city was incorporated in 1818 to distinguish it from Middletown in Jefferson County. The post office followed in 1819, giving the town a durable place on the county's mail map.

The city is small, and its older commercial core has a distinct architectural spread. A National Register account describes an approximately three-block district with Greek Revival, Italianate, and Victorian-era vernacular buildings, mixed with newer structures. That gives North Middletown a different scale from Paris while keeping it connected to Bourbon County's larger road and agricultural landscape. The Main Street area carries the practical marks of a crossroads town: a compact business strip, routes leading toward nearby county centers, and a name that records how local geography and postal naming shaped the community.