Challenge Trails

Discover the unique beauty and flavors of Winchester, Kentucky, through our exciting “Challenge Trails.” The Beer Cheese Trail® invites visitors to explore local eateries and breweries while savoring this beloved Kentucky delicacy. With a digital passport in hand, participants can sample delicious recipes from each stop and unlock fun prizes, making it a delightful culinary adventure.

Venture into history with the Kentucky Capital Quest, where you can learn about Winchester’s rich heritage as the “Beer Cheese Capital of the World” while navigating through its landmarks.

For those looking for a taste of the region’s spirits, the Moonshine Trail offers a glimpse into the art of moonshining, showcasing local distilleries that celebrate this time-honored tradition, including Winchester’s very own Regeneration Distillery.

Each trail provides a unique perspective on Winchester and Clark County, highlighting its place among Kentucky’s most fascinating destinations. Stay tuned for future plans, including the Daniel Boone Historic Passport and an Attractions Passport for Winchester, which will further enhance your exploration of our vibrant community and its storied past.