A great place to hang out and grab a few locally-made craft beers and cocktails while you're in town! Located on historic Depot Street!

Located on historic Main Street in Downtown Winchester, the ultimate destination for community, coffee, and unforgettable late nights! As you step into this space, you'll be greeted by the enticing aroma of freshly brewed coffee, creating an inviting atmosphere where friendships are forged and memories are made. Best coffee in town! Also serve cocktails and locally-made craft beer later in the day.

Housed in the historic Guerrant Mission Clinic and Hospital, the Bluegrass Heritage Museum highlights local history through engaging and innovative exhibits that explore the rich cultural heritage of Kentucky’s Bluegrass Region.

One of the coolest places in town!

Best tacos, birria, margaritas, cocktails, and service in town with an authentic Mexican atmosphere! Not your average small-town Mexican restaurant.

"Located in Downtown Winchester, Kentucky we are honored to serve our Central Kentucky patrons. Refined, yet familiar, we strive to offer you the ambiance and taste of true Southern charm. Our recipes are as strong as the historic bricks which house them." Large cocktail bar available and the best apps in town!

Housed in an 1885 original horse-drawn fire station, they serve Winchester, KY delicious pizzas, paninis, craft beer, specialty cocktails, and host a variety of music and entertainment.

This 30-acre public park has a two-acre adventure play area, nature trails, walking paths, dog parks, and open lawns.

The park design is inclusive with an ADA-accessible paved walking path throughout and a play area with options for children of all abilities. Open from dawn to dusk.

Founded and bottled in Winchester since 1926, “Ale-8” is the only soft drink invented in Kentucky still in existence. Deemed “Kentucky’s Official Soft Drink,” this ginger and citrus flavored soda was inspired by ginger-based recipes from northern Europe. Ale-8 can be described as a ginger soft drink with a “kick.” Factory tours are available by appointment!

Inspired by the connection between food, wine and hospitality since its opening in 2006, Harkness Edwards Vineyards offers a tasting room, breathtaking views, vineyards, gardens and more. Owned and operated by the Edwards family, the vineyard offers a distinctive sense of love and passion shown through their artisan-made wine.