Compiled as an act of love by the amateur historian J. Winston "Squire" Coleman, a lifelong resident of the Lexington area, the book offers bits of Bluegrass as well as national history. Along with his focus on the development of stagecoach travel, the author covers period details such as pioneer roads, taverns, conflicts among drivers, travelers' adventures, mail carriers, turnpikes and tollways, and the coming of the railroad. Celebrities who crossed the Bluegrass by stage included statesman Henry Clay, singer Jenny Lind, gambler Sam Austin, and abolitionist Delia Webster.
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