After service in Gen. Braxton Bragg's Kentucky Campaign and at the Battle of Perryville, Col. John Hunt Morgan's Kentucku cavalry joined Lt. Gen. E. Kiby Smith's portion of the Army of Tennessee on its retreat out of Kentucky. On October 15th, while the army sat 25 miles southeast of Richmond, Kentucky, Morgan proposed to Smith that his cavalry raid behind Union lines, disrupting railroads and supply routes, thus hampering the Union's timid pursuit of the main Confederate force. Smith agreed to Morgan's plan.
Leaving their camp southeast of Richmond on the 17th, Morgan's force traveled northwest, took the lightly defended town of Lexington on the 18th, then left in early afternoon for Versailles to the west. For the next 12 days, passing west and south in a wide arc, the raiders moved through Lawrenceburg, Bloomfield, Bardstown, Elizabethville, and Litchfield. They crossed the Green River between Woodbury and Morgantown, and the Muddy River south of Rochester, then rode toward Greeneville and Hopkinsville, reaching the latter around the 25th. Union pursuit of Morgan was negligible after Lawrenceburg and Bloomfield, and ceased almost completely after the Confederates crossed the Muddy. Morgan called a 3-day halt at Hopkinsville, where his troops were fed by sympathetic citizens and did minor damage to railroads and bridges before setting out for Tennessee.
The men rode into Springfield in north-central Tennessee on November 1st. Though they later pressed on to Gallatin in the east, the raid effectively ended when they crossed the state line. The raiding party, made up of the 2nd Kentucky Cavalry, under the subordinate command of Lt. Col. Basil W. Duke, Col. Richard M. Gano's 3rd Kentucky Cavalry, and a Kentucky cavalry battalion led by Maj. William C. Breckinridge, took and paroled several prisoners and sustained few casaulties. The minor operation served to keep Federals insecure in the Blue Grass state.