What to do and see in Winchester, Kentucky (KY): The Best Sights & Landmarks

March 3, 2022 Flossie Demartino

Winchester is a home rule-class city in and the county seat of Clark County, Kentucky, United States. The population was 18,368 at the 2010 census. It is part of the Lexington-Fayette, KY Metropolitan Statistical Area.
Restaurants in Winchester

1. Clark Mansion aka Holly Rood

28 Beckner St, Winchester, KY 40391-1810 http://hollyroodevents.com
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4.5 based on 2 reviews

Built in 1814 by James Clark, 13th Governor of Kentucky, the house follows the simple lines of Federal style architecture. Tours by appointment.

2. Scenes from the Kentucky River Mural

1240 Ford Road, Winchester, KY 40391 +1 859-744-0556 [email protected] http://www.tourwinchester.com/contact/scenes-from-the-kentucky-river-mural/
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Scenes from the Kentucky River Mural

Among the many reasons to visit the Civil War fort at Boonesboro is the impressive mural adjacent to the parking lot. The mural’s 12 colorful panels illustrate significant eras and events in the history of the area, including the era of Native Americans, Clark County’s first church, and commerce and industry through the centuries.

3. Historic Downtown Winchester

Winchester, KY 40391
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4.0 based on 10 reviews

Historic Downtown Winchester

Historic Winchester was placed on the National Register of Historic Places in 1981. The business district looks much as it did over a hundred years ago with the five globe lampposts and elevated sidewalk. Downtown is filled with quaint shops, wonderful restaurants and charming character. Enjoy a tour at your own pace. Stop by 2 Sotu Maple for a brochure with a map.

4. Civil War Fort at Boonesboro

1250 Ford Road, Winchester, KY 40391 +1 800-298-9105 http://www.civilwarfortatboonesboro.com
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3.5 based on 15 reviews

Civil War Fort at Boonesboro

The earthwork fortification was built by Union Soldiers to defend the ford and ferry at Boonesboro. A scenic trail provides a beautiful view of the Kentucky River. Self-guided tour. A moderately strenuous, wooded one-mile loop trail that provides panoramic views of the Kentucky River Valley. Pet friendly.

Reviewed By charlesbC6079KL

The gun battery never saw action and is actually at Ford, Kentucky, to guard the crossing here on the Kentucky River. Stiff walk up a hill to the gun battery but well worth the climb. Nearby is Fort Booneboro and Kentucky River Museum.

5. Winchester Cemetery

625 W Lexington Ave, Winchester, KY 40391-1369 +1 859-744-6889 http://www.interment.net/data/us/ky/clark/winchester.htm
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Winchester Cemetery

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