Tours & Trails
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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…
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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…
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Ale-8 One
Ale‑8 One, a beloved Kentucky classic, has its roots deeply planted in Winchester, where it’s been crafting its signature ginger and citrus soda since 1926. A local favorite, Ale‑8 One is not just a drink; it’s a tradition. With its crisp, and refreshing flavor, it’s the perfect companion for any occasion, whether you’re picnicking in…
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Civil War Cell Phone Tour
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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,…
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Abettor Brewing Company
Abettor Brewing Company is a craft brewery celebrated for its diverse and innovative beers and ciders. Known for its welcoming taproom and community events, it offers a friendly atmosphere perfect for enjoying unique brews and local gatherings. Tasty bites also are available from a food truck.
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Daniel Boone Heritage Trail
The Daniel Boone Heritage Trail is a historical and scenic route that commemorates the journeys and exploits of the famous American pioneer, Daniel Boone. This trail takes visitors through key locations that highlight Boone’s role in exploring and settling the Kentucky frontier in the late 18th century. Along the trail, you’ll fine markers and informational…
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Civil War Fort at Boonesboro Cell Phone Tour
A few simple instructions are all you need to start your audio tour. Audio stop numbers are displayed in your brochure and on audio tour signs. Simply enter the appropriate audio stop number on your cell phone keypad or enter star to advance to the next stop. To select a different tour please press zero.…
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Downtown Ride
The Downtown Ride highlights the Winchester Alley Tour, designed to take cyclists by downtown landmarks while avoiding heavy traffic.
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African American Heritage Trail
African American citizens of Winchester and Clark County have played a significant role in our community. In order to highlight some of our achievements, a group of volunteers got together to form the Winchester Black History & Heritage Committee in 2014. The group published the African American Pictorial History of Clark County, Kentucky in 2018.…
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Horse Farm Tours
Although Winchester is fortunate enough to be surrounded by many beautiful horse farms and breathtaking views of our four-legged friends, we do not have any local horse farm tours. However, don’t fret. Within thirty minutes or so from Winchester, you can easily find several farms that do offer tours.
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Loma’s at the Opera House
Lomas’s at the Opera House is a quaint eatery nestled within historic surroundings. Offering a blend of classic American fare and Southern comfort food, it’s renowned for its charming ambiance. Perfect for a casual meal or special occasion, Loma’s provides a delightful dining experience in the heart of Winchester.