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Kentucky was one of America’s legendary frontiers, thrown open when Daniel Boone blazed the Wilderness Road through Cumberland Gap just as the American Revolution was beginning. Until then, the formidable Appalachian Mountains had discouraged the colonists from even attempting to explore the virgin territory extolled by a few intrepid trappers and hunters — a land of deeply forested hills and valleys roamed by bears, buffaloes, and elk.
Kentucky was also a land of surpassing beauty and natural abundance, and Boone’s expedition suddenly made it attainable. Following his trail or traveling down the Ohio River, settlers poured into the new frontier from Virginia, the Carolinas, and Pennsylvania — 12,000 of them by the end of the Revolutionary War.
Bennett's Mill Covered Bridge, Kentucky

One of my favorite local landmarks is Bennett's Mill Covered Bridge, which crosses Tygarts Creek near the town of South Shore in northeast Kentucky.
Blue Heron Coal Mining Camp, Kentucky

A coal mine may not sound like it's worth a side trip, but Kentucky's Blue Heron Coal Mining Camp certainly is.
You can get there via the Big South Fork Scenic Railway, an open-air train based in the small town of Stearns. At its peak, the remote mine employed 300 men. Recordings in the "ghost structures" of the buildings describe the miners' lives, and mannequins illustrate the cramped conditions.
Columbus-Belmont State Park, Kentucky

I found a little-known bit of Civil War history at Columbus-Belmont State Park, atop a bluff overlooking the Mississippi River in Kentucky.
In an effort to stop Union ships, Confederate troops here stretched a huge chain across the river, anchored on each side by massive earthworks in Columbus, Kentucky and Belmont, Missouri. The river's strong currents quickly broke it.
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