Did You Know?

In March of 2022, we presented some fun and quirky facts about Winchester—truly an original among Kentucky towns with its early Daniel Boone ties, elevated downtown sidewalk, hemp history, geology quirks and Ale-8-One—the only soft drink invented in Kentucky still in existence. Here are more strange and unusual things to see, do and know about in the town that gifted the world with beer cheese:

Did you know. . .

. . .You can overnight in a place where horse-drawn buggies were once repaired at the Carriage Inn. Head up the staircase to the second floor of this historic building to find the charming one-bedroom apartment managed by Airbnb superhost Gary. Located in Winchester’s Downtown Historic District, it features views of the county courthouse and is right around the corner from Mason on Main, an always original Winchester shopping experience.

. . .All that’s left from Winchester’s last remaining brick street may be found on Depot Street, not far from where the Winchester/Clark County Farmers’ Market sets up shop, May through September. 

. . .Among the more than 60 veterans laid to rest at Winchester’s Daniel Grove Cemetery are Buffalo Soldiers, African Americans who joined the 9th and 10th U.S. Cavalries and the 23rd and 24th U.S. Infantries. Established by Congress as the first peacetime all-Black regiments in the U.S. Army, these soldiers served across the southwestern U.S. from 1866 to 1890. The unusual name was given to them by Native Americans in the late 1870s because, according to the National Park Service, “because of their dark, curly hair, which resembled a buffalo’s coat, and because of their fierce nature of fighting.”

. . .The peculiar structure referred to as the “Lightbulb” by local geologists and located not far from downtown Winchester is considered an excellent example of faulted, fractured and dolomitized Lexington limestone. It is found on the northwest side of a roadcut along KY 627, approximately 3.6 miles southwest of the intersection of KY 1958 and KY 627 and is so special that geologists from all over the country have come to see it.

. . .You can eat at Winchester’s original fire station on land deeded in 1885 to the Board of Councilmen of Winchester. Here, the Rough and Ready firefighters once occupied the first floor and the mayor along with the first volunteer library had the upstairs. The engine house was occupied until 1909 when a fire burned through an adjacent building. Fast forward a century to 1985 and Bob Tabor opening a deli in the space and then zoom another 35 years ahead to the opening of Engine House Pizza Pub, owned by Jill and Chad Walker. Drop in for a Hot Ham Hoagie or an artisanal pizza finished with a swirl.

. . .A nearly 100-year-old surgical suite gives a peek into medical practices of the 1930s when the Guerrant Clinic and Hospital Rooms operated in Winchester—in this very building, in fact, now home to the Bluegrass Heritage Museum. Check out the sink that was operated by foot pedals to avoid the risk of contaminating the hands and the large autoclave (also known as a steam sterilizer) used to sterilize operating tools.

. . .Couples planning their wedding can tie the knot in a showstopper of a place built 150 years ago as a gift for Winchester. The Winchester Opera House was built in 1873 by the town’s first mayor, James D. Simpson, who gave it to the city as a cultural center. One hundred thirty years later in 2003, the former performing arts facility was transformed into a majestic wedding venue—and so beautifully and historically preserved that it was recognized for its efforts. It features multiple ceremony locations and bridal suites on location and can also be booked for corporate events and other gatherings.

. . .Mark Twain tied to Winchester? Author Harry Enoch chases down the facts to the myth that the mother of “the greatest humorist the United States has produced,” Jane Lampton Clemens, was born in Winchester. Not so fast, says Enoch in Where in the World, Vol. 3, Historic People and Places in Clark County, Kentucky­, noting Jane was born in Adair County, KY. Still, plenty of her kin left a record of their time in Clark County, including James Lampton, who owned property in Winchester, including a tavern, and served briefly as a deputy sheriff. Find Enoch’s books at the Bluegrass Heritage Museum.

Autumn scenery in the Red River Gorge.

…Having Winchester as a homebase puts visitors within 35 minutes of Red River Gorge, one of the world’s top climbing and rappelling destinations. Hike, bike, climb, fish, picnic, take a scenic drive or view the wildlife in this wild and rugged federally-designated National Geological Area, National Natural Landmark and National Archaeological District that is listed on the National Register of Historic Places. Then relax in another National Register of Historic Places—downtown Winchester—at an uptown Airbnb, like the Artist’s Loft or Stylish Loft, in easy strolling distance to restaurants and shops.