Winchester, KY

Winchester is the county seat of Clark County, Kentucky, named after Winchester, Virginia. It has a historic Bluegrass-region feel, with courthouse streets, older homes, schools, and nearby farmland. The city's most memorable modern hook is the annual Beer Cheese Festival, held in June and rooted in a local food tradition that sounds odd until you are there eating it. Winchester feels like a working Kentucky county seat with a playful streak, close to Lexington but still distinctly its own town.