Welcome to the hidden gem of Middlesborough, Kentucky, founded in 1886! Nestled in the heart of the Appalachian Mountains, this dynamic town offers a blend of history, culture, and outdoor adventure. Explore the legacy of America’s 26th president, Theodore Roosevelt, who hunted in the nearby wilderness. With a population of around 13,561, Middlesborough has sister cities in both England and Japan, adding an international flair to this charming southern town.