Wandering Through Winchester, Kentucky

by Nicky Reynolds

In the late 1700s, traveling took a lot longer and was much more treacherous than it is today, but our ancestors would saddle up the horses, load up the caravan, and traverse the mountains and valleys of this great country in hopes of discovering the perfect terrain for new towns and cities. One well-known historical figure who developed a reputation for such discoveries was Daniel Boone.

Like many families who relocated to the United States during his time, Daniel Boone’s father left England to escape religious persecution. He was a Quaker who settled in Pennsylvania and later moved to North Carolina. Daniel Boone is most well-known for his trek through the Cumberland Gap, which came to be called the Wilderness Road, though much of his lifetime work included land surveying for other men who were trying to find properties to which to move.

In the late 1760s, Boone was doing just that when he took his first glimpse of the Bluegrass region of what is now known as Winchester, Kentucky. Today, “Boone’s Overlook” is a popular destination for hikers, birdwatchers, and history buffs. The challenging 730foot elevation to the top of Pilot Knob State Nature Preserve provides an impeccable view of rolling ridges and flat farmlands.

Fort Boonesborough State Park is another attraction worthy of a visit. Located on the Kentucky River, it is the site built in 1775 by Boone and his men. Today, visitors can view the reconstructed fort, explore trails, stay at the campgrounds, and learn more through living history programs.

To walk in his footsteps, one need only traverse the Daniel Boone Heritage Trail, one of Kentucky’s official Scenic Byways. The route, established by Boone in 1775, begins at Fort Boonesborough and ends in Athens near Boone’s Station, which he settled in 1779.

In the 1700s and 1800s, Scottish immigrants built miles of stone fences which can be seen on many farms and pastures across the area.

The Holly Rood—Clark Mansion was built in 1814 by James Clark, the 13th governor of Kentucky. The Federal-style home is open for tours by appointment.

For more information on Daniel Boone’s history or the Winchester, Kentucky area, contact the WinchesterClark County Tourism Commission at 800-298-9105 or log on to visitwinchesterky.com.

About The Author Nicky Reynolds is a freelance writer who lives in East Tennessee with her 2-year-old daughter and their beloved rescue, Molly. Her dreams are to explore Italy, move to Hawaii, and keep adding new stamps to her passport.