Confederate Brigadier General John Hunt Morgan and his raiders arrived in Chester around 1 pm on July 18, 1863, after a grueling ride across Meigs County. Knowing that Union forces were close behind, Morgan expected an attack at any moment. Crossing the Shade River into Chester, the Confederates burned the bridge to delay pursuing Union forces. The fire soon spread to a local mill that housed most of Chester's grain and lumber supply. During the confusion, Morgan's local guide slipped away. As the Confederates needed another guide to get to the river crossing at Portland, less than 20 miles away, the resulting search delayed them for more than 90 minutes in Chester. Morgan and his troops used the search for a new guide as chance to rest, feed their horses, and refill their canteens. The July heat took a toll on the exhausted men and horses that welcomed a momentary respite. The Confederates rested on the commons across from the old county courthouse and the Chester Academy on the hill. "Our troubles are over," Morgan was reported to say while waiting on the porch of a nearby house. "Tomorrow we will be on Southern soil." After finding a guide, Morgan and his men headed out to the ford at Buffington Island.