In 1861, the Southern Confederacy is formed, and the American Civil War ignites. While the official military campaigns are being fought miles away, the pro-Southern Bushwhackers engage in guerrilla warfare on the back roads and across the countryside. Along the Kansas/Missouri border, childhood friends Jake Roedel Jobey Maguire), the Missouri-raised son of a poor German immigrant, and Jack Bull Chiles (Skeet Ulrich), the son of a Missouri plantation owner, join up as Bushwhackers. These young men are, or must quickly learn to be, skilled gunmen and expert horsemen executing daring raids on the North’s Union soldiers and sympathizers.

With a harsh winter looming, the Bushwhackers must disperse and find shelter. Several squad members hole up in a hidden hillside dugout. Their vigil is brightened by the visits of compassionate young widow Sue Lee (Jewel). Then, the realities of the war intrude, splintering the group but uniting Jake and Holt in solidarity as outsiders. When the seasons change and the brutal battles intensify, the young men reach turning points both in the fighting and in themselves.