Depending on one's point of view, Cynthiana was the location for two, or possibly four, battles during the Civil War. In July 1862, during John H. Morgan's summer raid, there was fighting that took place mostly in town located around the covered bridge, along the Licking River, and downtown. On Morgan's last raid of 1864, fighting occurred in and near Cynthiana on June 11th and 12th. June 11th saw fighting near the covered bridge, the railroad depot, the New Rankin Hotel, parts of downtown, while later fighting occurred near Keller's Bridge. The next day the fighting was initially centered along the Millersburg Pike (Kimbrough Hill and what is now Battle Grove Cemetery) and then towards McGee Hill, before the Confederates were routed and chased into town.
Learn more about the 1862 battle
Learn more about the 1864 battle(s)
And if you are really wanting to learn even more, purchase Bill Penn's excellent Kentucky Rebel Town: The Civil War Battles of Cynthiana and Harrison County at Amazon.