US 68 cuts through the western part of Boyle County, running generally northeast through some typical rolling Central Kentucky terrain from Marion County. It intersects with US 150 in downtown Perryville before continuing northeast into Mercer County. South of Perryville it is known as the Lebanon Road and northeast of town it is known as Harrodsburg Road.
As the route approaches Perryville it passes over some ground that saw skirmishing between Union and Confederate forces on October 8, 1862, as a sideshow to the Battle of Perryville. Confederate cavalry under General Joseph Wheeler held off Federal forces under Thomas Crittenden most of the day before withdrawing into town.
Perryville itself was first settled in the 1770s, and since 1817 has been incorporated as a city. It features one of the most intact 19th Century streetscapes in the United States - Merchant's Row, which fronts US 68. Most of these buildings date from the 1840s, and a public-private partnership (the Perryville Enhancement Project) is working to preserve and interpret these structures.
The city has connections to such notables as prohbitionist Carrie Nation, singer-songwriter Kendall Hays, Pulitzer Prize-winning photographer Moneta Sleet, singer Eddie Montgomery, and actor George Clooney.
Perryville was also the site of Kentucky's largest and bloodiest battle on October 8, 1862. The battle was fought between Don Carlos Buell’s Federal Army of the Ohio (55,000 men) and Braxton Bragg’s Confederate Army of Mississippi (16,000 men). After some initial skirmishing west of town, the Confederates attacked the Federal left wing at 2 PM.
Their ferocious offensive drove the Union troops back after five hours of heavy fighting. Late in the afternoon other Federal troops pushed into Perryville and fought in the streets. That night Bragg, hopelessly outnumbered, began a retreat that did not end until his army was back in Tennessee. During the battle, 7,500 men were killed, wounded, or missing, one of the worst per-hour casualty rates of the Civil War.
The battle ranks as Kentucky’s largest and bloodiest, and Kentuckians distinguished themselves on both sides. It is also critical to the state’s history; after this battle, Kentucky was secured firmly in Union control for the rest of the war.
Today the battlefield area is preserved by the Perryville Battlefield State Historic Site (founded 1928), located 2 miles outside of town. It has been a National Historic Landmark since 1961, and the City of Perryville has been a National Register Historic District since 1973. US 68 through Boyle County is a State Scenic Byway.