Confederate Major General Sterling Price eyes a ford on the Big Blue River as a strategic crossing for his 500 wagons of supplies. After winning back-to-back victories at Glasgow, Lexington, the Little Blue River, and Independence, Price's strategic position in northwest Missouri grows precarious as Union Generals Samuel R. Curtis and Alfred Pleasonton threaten to trap Price between them. At Byram's Ford on the Big Blue River, Union Major General James G. Blunt defends the west bank of the river. Confederate Brigadier General Joseph O. Shelby attacks and outflanks Blunt's defenders, causing the Union forces to fall back to Westport. Price successfully crosses the river and advances to the town of Little Santa Fe. The following day, on October 23, Union General Pleasanton attacks Confederate Brigadier General John S. Marmaduke's forces, who are attempting to hold Byram's Ford to protect Price's rear. Around 11:00am, the Confederates lose Byram's Ford and regroup as one force. The consolidated Confederate force falls under attack by Union Major General James G. Blunt, and what will become known as the Battle of Westport ensues.

On October 23, the Battle of Westport, or the "Gettysburg of the West," begins with Sterling Price's Army of Missouri trapped between the forces of Generals Curtis and Blunt (just south of Westport, along Brush Creek), Pleasanton (crossing the Big Blue River from the east), J. Hobart Ford and Colonel Charles "Doc" Jennison. Outnumbered 3-to-1, Price decides first to advance toward Curtis and Blunt at Westport. Blunt's Union skirmishers cross Brush Creek but are turned back by a Confederate attack led by Generals Joseph O. Shelby and James Fagan. The Confederates advance to the streets of Westport, but the tides of battle reverse as Pleasonton advances over the Big Blue River and Curtis leads his reinforcements in a counterattack back across Brush Creek. After more fighting, Curtis and the Union Army triumph in the largest Civil War battle west of the Mississippi River. General Price retreats, marking the end of Confederate military ambitions in Missouri and the last major Confederate raid into a Union state.