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Fincastle was established in 1770, the same year the Boston Massacre lit the spark that became the American Revolution. The town was listed in the National Register of Historic Places in 1969 – the year Neil Armstrong walked on the moon. During the intervening two centuries, Fincastle was a bustling western outpost, a hive of taverns, saddle shops, millers, livery stables, chair and furniture makers, blacksmiths, wheelwrights, and a blue dyer (blue being the most elegant and expensive color of the day). Fincastle was the last stop on the Great Wilderness Road to the west.

This Big Spring was one of the many reasons this area was an Indian crossroad, and, later, one for settlers. It was a gathering place and a source for water. It’s doorway, Jockey Alley (now Back Street), was where horses were traded, bet on, and raced.

The town was incorporated in 1772 as the seat of half of the Northwest Territory, reaching all the way to what is now Wisconsin. The House of Burgesses Act authorizing that expanse of county stated that those folks living on the “Mississippi waters” need not pay any levies needed for the building of the courthouse, due to their distance.


In 1818, Thomas Jefferson provided drawings for a brick courthouse, which replaced the original log one. It burned in 1870, as did many original homes on Main Street, was re-built, and was burned and re-built again in 1970, again by Jefferson’s plans.

The 1874 taxpayer lists identified 59 buildings, 26 log dwelling houses (many still extant, some covered now with siding), and 11 frame houses. Agriculture, with it’s handsome “plantation” homes, was a major business in the area during the next three-quarters of a century, and Fincastle provided it’s focus, entertainment, and business center.

The Civil War had little effect on Fincastle, other than the region wide decline in resources. During the late 1800’s, Fincastle became a tourist attraction; visitors came to “take the waters” and their ease in the cooler mountain air.


During the last century and today, Fincastle remains the county seat, with all the government and legal activities that involves. The town has now settled into her skirts, and is a friendly, comfortable town rich with architectural styles covering two centuries.

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