Tours & Trails

There are countless ways to experience Winchester, Kentucky, through its landscapes, flavors, and stories. Hike up to Pilot Knob State Nature Preserve and imagine the awe Daniel Boone felt in 1769, gazing over Kentucky’s Bluegrass region. Drive scenic, winding roads through Civil War history, cycle the historic downtown’s alleyways, or take a quiet cemetery tour to connect with the past.

Explore the John Holder Trail in Lower Howard’s Creek Nature and Heritage Preserve, or follow the African American Heritage Trail to hear inspiring tales like that of Fanny Cole, then enjoy a hard apple cider named in her honor at a local brewery. Winchester’s tastes are equally adventurous: sip farm-to-bottle moonshine, enjoy a flight of locally crafted beer, or raise a glass of wine—sweet, dry, or big and bold—overlooking a lush vineyard. When you’re ready to recharge, grab a cup of Arabica-bean coffee roasted fresh at the local roastery, and savor every flavor Winchester has to offer.