Challenge Trails

  • Moonshine Trail

    Embark on a journey of authentic flavor and rich history at Winchester’s own Regeneration Distillery—a must-visit stop on Kentucky’s Moonshine Trail! Step into a hidden world where passion and craftsmanship collide, offering a taste of Kentucky’s untamed spirit in its purest form. At Regeneration Distillery, the Moonshine Trail comes alive as you’re invited to experience unaged…

  • KY Capitals Quest

    The Beer Cheese Capital of the World! As an important part of the overall Bluegrass region, Winchester proudly holds the prestigious title of the Beer Cheese Capital, inviting visitors on a culinary journey like no other. Join us in experiencing the rich flavors and heritage of our renowned beer cheese, where tradition meets innovation to…

  • Beer Cheese Trail®

    We proudly host fifteen beer cheese stops, plus the annual Beer Cheese Festival – held the second Saturday each June. Held in historic Downtown Winchester, the Festival celebrates commercial and amateur beer cheese makers and offers food, drink, and entertainment for the entire family, plus a wide variety of local arts and crafts vendors. And,…