Putnam County was a divided land during the Civil War as local residents enlisted in either Federal or Confederate units. It also was a crossroads, as both armies passed through the county numerous times over such important historic roads as the Walton Road (east-west route) and the Old Kentucky Road (north-south route). Although no major engagement by army regulars took place in Putnam County, forage raids, conscript sweeps, bushwhacking, and small skirmishes were typical occurrences. During a reconnaissance expedition, Union Col. Henry K. McConnell's troops killed 23 Confederate partisans and captured another 40 near Cookeville. The Battle of Dug Hill on February 24, 1863, was the most famous engagement in Putnam County. Confederate Col. John M. Hughs's rangers ambushed a detachment of Col. William B. Stokes's 5th Tennessee Cavalry along the Calfkiller River and killed more than 40 men.
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