6 Best Things to Do in Winchester, Kentucky

By VI Staff on September 7, 2021 - Updated

The City of Winchester

The town of Winchester, Kentucky is known for being a place for “original, local experiences,” ranging from hand-on history to Ale-8 and much more. Located just outside of Lexington, the town is a unique one, the place where Kentucky’s “official soft drink,” Ale-8, was founded along with the idea of beer cheese. The town even hosts the annual Beer Cheese Festival and is home to a Beer Cheese Trail. There’s much more to Winchester, however, than food and drinks, including museums, art, preserved geological areas, historic sites, and more. Certain attractions may be temporarily closed or require advance reservations. Some restaurants are currently offering pickup only. Hours/availability may have changed.

1.Red River Gorge Geological Area

The Red River Gorge Geological Area is a scenic area within the Daniel Boone National Forest near Winchester, Kentucky. Known for its abundant geological formations, the area features amazing towering sandstone cliffs, unusual rock formations, and many natural stone arches. Designated by the United States Forest Service as a national geological area, the Red River Gorge attracts visitors with its opportunities for outdoor recreation throughout the entire year as well, such as wildlife viewing, canoeing, camping, hiking, and other activities. The Red River Gorge area is also designated as a National Archaeological District and a National Natural Landmark.

3451 Sky Bridge Rd, Stanton, KY 40380, Phone: 606-663-8100

2.Bluegrass Heritage Museum, Winchester, Kentucky

The Bluegrass Heritage Museum is a place that brings the Bluegrass region’s history to life through its collection, preservation, and exhibition of objects associated with the history of Winchester, Kentucky, as well as the surrounding Clark County and Bluegrass area of the state. The unique museum highlights the history of the Bluegrass region’s places and people, from the settlements of the Eskippakithiki Indian up through the present day. The first Western frontier of America, the area attracted a number of colorful characters, such as Simon Kenton and Daniel Boone. In addition to the many exhibits, there is also a gift shop.

217 S Main St, Winchester, KY 40391, Phone: 859-745-1358

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3.Lower Howard's Creek Nature and Heritage Preserve, Winchester, KY

Lower Howard's Creek Nature and Heritage Preserve was established in November of 2000 as the fortieth state nature preserve in Kentucky, featuring many miles of nature trail winding through several historic sites and allowing hikers to view an array of animal and plant species. Guided tours of the preserve are offered by appointment as well. The preserve encompasses more than 300 acres of land along both sides of the scenic Lower Howard’s Creek and was created to preserve threatened and endangered species, preserve and interpret the history of the Bluegrass Region and Clark County, and to provide nature education.

1225 Athens Boonesboro Rd, Winchester, KY 40391, Phone: 859-806-2466

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4.Leeds Center for the Arts, Winchester, Kentucky

Situated in the middle of downtown Winchester, the Leeds Center for the Arts has been a part of the local community since 1925. The historic theater hosts a variety of community and cultural events throughout the year, including educational classes, concerts, musicals, and plays. The Leeds Theater was one of the first movie houses to open in Winchester, Kentucky in May of 1925. The theater eventually closed in 1986, but was restored by the Winchester Council for the Arts and reopened as the Leeds Center for the Arts in 1990. Today, the center hosts events and shows classic movies.

37 N Main St, Winchester, KY 40391, Phone: 859-744-6437

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5.Clark Mansion aka Holly Rood, Winchester, Kentucky

The Clark Mansion, or also known as Holly Rood, is a Federal-style house built by Kentucky’s thirteenth Governor, James Clark, back in 1813 and 1814. One of the most historic houses in Clark County, the home today is full of a variety of mementos and antiques that help share the local community’s story. In 1974, Holly Rood was added to the country’s National Register of Historic Places. Now owned and operated by the local government, visitors can take a tour of the Clark Mansion by appointment. The building is also often used for special events, such as weddings.

28 Beckner St, Winchester, KY 40391, Phone: 859-745-6664

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6.Cairn Coffee House, Winchester, Kentucky

A “small town coffee shop” that has a big heart, the Cairn Coffee House has a main mission of serving others and adding value to the town of Winchester, Kentucky. A non-profit and faith-based organization, the coffee shop is located across from the Courthouse on Main Street and was originally owned by the Calvary Christian Church. Since it opened in 2012, The Cairn has become a “landmark” for Winchester. The coffee shop is located on the first floor of the building, offering an array of specialty coffee beverages, light food options for breakfast, lunch and dinner, and an assortment of gelato.

17 South Main St, Winchester KY 40391, Phone: 859-737-2000

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