Dillion “Old Dill” Asher was one of the early pioneers of southeastern Kentucky, a frontier soldier and farmer who became the toll keeper at the Cumberland River ford at what’s now Pineville, giving him a front row seat to the early settlement of the state.
In this episode, we tell Old Dill’s story, from his connection to the first settlers in what became Tennessee, his military service, his journeys into Kentucky along the Wilderness Road, the settlement of Red Bird Valley, and his, shall we say, “complicated family life.”
Along the way, we try to separate what can be documented from the rich folklore that grew up around one of eastern Kentucky’s most colorful pioneers.
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