Home of Kentucky’s Official Soft Drink, Ale-8-One, and the birthplace of beer cheese, Winchester, Kentucky, is all about being original. Whether you’re touring the site of a Civil War earthen fort, dining in a historic fire station or shopping for eclectic antiques, this charming town in Central Kentucky is simply one of a kind.
Welcome to Winchester.
Outdoors & Recreation
From historical sites to nature preserves, Winchester is a gold mine for outdoor enthusiasts with its hiking trails, gorges, and expansive forests. Spend the night camping under the stars, or keep your eyes peeled birdwatching – you may spot a wild turkey (or two). For a dose of Civil War history, visit the remains of an original Civil War earthen fort and take in the panoramic views of the Kentucky River Valley.
If you’re looking for a quiet escape from the hustle and bustle of the city, visit Lower Howard’s Creek Nature and Heritage Preserve. Capturing the beauty of Kentucky’s Bluegrass Region, this preserve is home to scenic trails, cascading waterfalls and historical sites (as well as 400 species of rare flora and fauna exclusive to the region). Hike on the John Holder Trail (the only portion of the reserve open to the public) or book an organized guided hike to see other areas of the preserve and pioneer-era historic sites.
Winchester also offers convenient access to the breathtaking Red River Gorge. Just a thirty-minute drive away, this natural wonder is known for its stunning geological formations, diverse flora and fauna, and numerous recreational opportunities. Embark on exhilarating adventures like rock climbing, ziplining, mountain biking, underground kayak tours and crossing a 78-foot sandstone rock bridge. Extend your stay by camping overnight or renting one of the cozy on-site cabins or treehouses.
Food and Drink
Whether you’re craving authentic Italian or farm-to-table cuisine, Winchester serves up a variety of delicious dining options. Grab a burger or wings at DJ’s Steakhouse Bar & Grill, a local favorite known for its friendly atmosphere, mouthwatering bar grub (order the pretzels with warm beer cheese), and various craft beers on tap. Love pizza? Head over to The Engine House, a family-friendly pizzeria located in a former fire station serving an expansive menu of pizzas, salads, subs, calzones and strombolis.
Experience riverside dining at Halls on the River, a rustic restaurant and tavern. Relax on the deck as the Kentucky River rolls by and dine on Southern-inspired dishes, seafood and steak. Try the Famous Hot Brown, a Kentucky classic featuring a roasted turkey sandwich piled high with bacon and tomatoes, smothered in cheese sauce and served in a piping hot skillet!
For a taste of local flavors, visit Laura’s Mercantile! Discover everything from regional specialties and locally sourced ground beef to a selection of CBD and hemp products, including vegan hemp chocolate! Pick up other goodies like organic apple butter, tasty aged honey and herbal teas.
Cheese lovers unite! Winchester is the birthplace of beer cheese and home to the Beer Cheese Trail. Visit fifteen local establishments that craft this tangy and savory Kentucky specialty and sample different variations, from the award-winning gluten-free beer cheese at Full Circle Market to the drool-worthy beer cheeseburger at Smokin’ Howards. Be sure to sign up for the Digital Passport beforehand to earn swag for every stop you hit along the way.
Local Attractions
Searching for unique local attractions? Winchester has them in spades. Grab a bottle or case of Kentucky’s iconic soft drink at the Ale-8-One Bottling Company Store. You’ll understand why it’s a regional favorite with its sweet notes of ginger and citrus!
Considered one of Kentucky’s most historic and scenic roads, the Daniel Boone Heritage Trail begins across the river Fort Boonesborough and ends near Boone Station in Athens. Drive along this scenic byway and see the picturesque landscapes that played a role in the life of Daniel Boone, from the Boonesboro Quarry to the limestone cliffs of the Kentucky River Palisades.
Delve into the rich heritage of the Bluegrass region through exhibits that showcase the history of Winchester and its surrounding communities at the Bluegrass Heritage Museum. Here, you’ll find displays featuring artifacts, such as 19th-century farming equipment, hand-stitched quilts, Old World phone booths, and Civil War memorabilia. Stop by the gift shop and pick up a local history book before you go!
Shopping, Arts, & Downtown Charm
There’s no better place to shop until you drop than Winchester’s charming downtown area. Browse various boutique stores and specialty shops and explore a diverse range of products, from handmade crafts to fashion items. Shop for trendy clothing at The HighSide Boutique, discover quirky finds at Weird Owlz Vintage or pick up unique antiques at The Old Red Barn Mall.
Downtown Winchester is also home to a vibrant arts scene where local galleries showcase the work of talented regional artists. From contemporary pieces to traditional crafts, the art scene contributes to the area’s cultural richness, providing a visual feast for residents and visitors alike. Check out popular spots like Arts on Main Street for stunning paintings and textiles or Eve’s Uniques for an eclectic selection of home décor and artwork.
While in town, catch a live show at the historic Leeds Center for the Arts. From humble beginnings as a single-screen theater in 1925 to a diverse performing arts center in the heart of Winchester, the Leeds Center is the crown jewel of Main Street. Serving as a focal point for local entertainment, the meticulously restored venue hosts theater productions, concerts, comedy shows, and community events every week.
