The 16th Ohio, with Morgan's 7th Division, after just 11 hours rest, resumed their march at 4:00am. The Rebels had been hard at work placing obstacles all along the way, desperately trying to slow the Union troops so the Rebel infantry could catch up with them. Seven different blockades were encountered and overcome, and a road was built around a bridge that had been burned. At this bridge Morgan's advance troops came upon the blockaders and attacked them sharply. Two prisoners were captured, one of whom, a captain, was splendidly mounted and equipped.

During the day, a captain in a Tennessee regiment was shot through both lungs by a bushwhacker, small gangs of whom had begun to harass the column night and day.

Morgan's men marched as fast as possible and for a grueling 22 hours, not halting until 2:00am the next morning (October 2). The men slept in the woods along side the road. They were now just about a mile from Grayson, Kentucky.