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Battle of Westport Overview

The Battle of the Westport took place over a three-day period in October 1864. It all started on October 21, about 6 miles northeast of Independence, Missouri, on the Little Blue River. There around 8:00 a.m. on a cold Friday morning, a division of Confederate cavalry attacked a regiment of Federal volunteers defending a covered bridge across the Little Blue River. The fighting continued until mid-afternoon on Sunday, October 23, on the prairie south of Westport. Due to the number of soldiers involved, the Battle of Westport went down in history as the largest battle west of the Mississippi River during the American Civil War.

The confrontation south of Westport was the result of a three-year-long quest by Missouri Confederates to take their state back from Missouri Unionists and Federal occupying forces. Driven out of Missouri during the winter of 1861/62, Maj. Gen. Sterling Price had been fighting Union forces for three long years and desperately wanted to lead one last attempt to reclaim his home state of Missouri for the Confederacy. On July 23, 1864, Price wrote a letter to his commanding officer, Lt. Gen. Kirby Smith.

The Confederate flag floats over nearly all the principal towns of North Missouri, and large guerrilla parties are formed and operating in the southern portion of the State … I respectfully but urgently suggest the propriety of making a move into the State.

Price was not the only person urging General Smith to authorize an invasion of Missouri. So, on August 4, Smith issued orders to Price to launch an invasion into Missouri.

You will make immediate arrangements for a movement into Missouri, with the entire cavalry force of your district … Rally the loyal men of Missouri, and remember that our great want is men, and that your object should be, if you cannot maintain yourself in that country, to bring as large an accession as possible to our force … Make Saint Louis the objective point of your movement, which, if rapidly made, will put you in possession of that place … Should you be compelled to withdraw from the State, make your retreat through Kansas and the Indian Territory, sweeping that country of its mules, horses, cattle, and military supplies of all kinds.

Price named his invasion force the Army of Missouri, consisting of about 12,000 cavalry, although Price reported to headquarters that 4,000 of them were unarmed. The army included 14 pieces of field artillery. There were three divisions commanded by Maj. Gen. James F. Fagan, Maj. Gen. John S. Marmaduke and Brig. Gen. Jo Shelby. Leaving from Pocahontas, Arkansas, Price’s army entered the State of Missouri on September 19, 1864. Over the next month Price’s Army of Missouri left a path of destruction in his wake as he headed west to-ward Kansas.


The Federal commander in the Department of the Missouri, Maj. Gen. William S. Rosecrans, kept hearing rumors about an invasion of Missouri by Sterling Price. When Rosecrans finally learned that Price had entered southeastern Missouri, he ordered Brig. Gen. Thomas Ewing, Jr. to proceed with reinforcements down to Fort Davidson in Pilot Knob, Missouri. He also ordered his commanders in Springfield and Rolla to bring as much of their cavalry as possible and head for Jefferson City as quickly as possible.

The Federal commander in Kansas, Maj. Gen. Samuel R. Curtis, also heard the invasions rumors and kept in touch with Rosecrans. Curtis had even fewer troops to protect Kansas than Rosecrans had in Missouri. By the end of September, Curtis convinced Kansas Gov. Thomas Carney to call out the state militia. Curtis also ordered his second-in-command, Maj. Gen. James G. Blunt, to bring his veteran cavalry troops east to the Missouri border.


The stage was set. Rosecrans was mobilizing troops to defend Missouri, and Curtis was mobilizing his forces to defend Kansas. Price’s advance on St. Louis was delayed when he decided to attack the Federal garrison at Fort Davidson in Pilot Knob, Missouri. By the time Price moved north toward St. Louis, he dis-covered it was too well defended to attack. So, Price turned west, setting his sights on Jefferson City, the state capital. The Army of Missouri moved slowly west, collecting plunder and destroying infrastructure. The Confederates reached the outskirts of Jefferson City on October 6. Once again, Rosecrans had time to mobilize reinforcements, and Price decided not to attack Jefferson City. The Confederates continued marching northwest toward Boonville, located further up the Missouri River.

Now that Jefferson City was safe, Rosecrans ordered his second-in-command, Maj. Gen. Alfred Pleasonton, to assume command of the Federal cavalry and take out after the Confederate army. Rosecrans and Pleasonton named this ad hoc force the Provisional Cavalry Division, Department of the Missouri. His division held three brigades of Missouri State Militia cavalry, a force of around 4,100 troops. The commanders of the 1st, 2d, and 3d Brigades were Brig. Gen. Egbert G. Brown, Brig. Gen. John McNeil and Brig. Gen. John B. Sanborn, respectively.

Pleasonton planned to “proceed as a corps of observation after the enemy, to harass and delay [Price] as much as possible until other troops could be brought forward.”


With Price headed his way, General Curtis readied his defenses. Close to 15,000 Kansans answered the call to serve as state militia. Around October 15, General Curtis organized the Army of the Border into two divisions. The 1st Division, commanded by General Blunt, consisted of three brigades of Federal volunteer cavalry and one brigade of Kansas State Militia. Col. Charles R. Jennison (1st), Col. Thomas Moonlight (2d), Col. Charles W. Blair (3d) and Col. James H. Ford (4th) were appointed brigade commanders. The 2d Division consisted of Kansas State Militia under the command of Maj. Gen. George W. Deitzler.

Curtis ordered Blunt into Missouri with about 2,000 veteran cavalry. Blunt reached Lexington the day before Price’s advance did. Blunt was trying to buy time for Curtis to complete the Federal defense line back near Kansas City. Curtis decided to set up his main line of defense along the Big Blue River just east of Kansas City and Westport. He put the militia to work digging entrenchments around Wyandotte, Kansas, and Kansas City, Missouri, and along the Big Blue River.

The Big Blue [River] should be a first main line of battle, Kansas City a second, and finally, if overpowered, Wyandotte, on the north side of the Kansas River … I directed my chief engineer to construct fieldworks at each of these positions.

Around 11:00 a.m. on October 19, the Confederate advance ran into Blunt’s pickets just south and east of Lexington. Colonel Moonlight, 11th Kansas Cavalry, described the fighting that took place on October 19.

We held our ground for a couple of hours, checking his advance and sparring for time. A retreat was ordered in the direction of Independence … On the rebels came … [we] contested every inch of ground, fighting hand-to-hand with the advancing & flanking forces, never yielding [our] position until ordered.


Having scouted the area on his way to Lexington, General Blunt was convinced that the Federals could defend the covered bridge over the Little Blue River on the Lexington-Independence Road. He assembled his men there to wait for the Confederate advance. On October 21, Price ordered General Marmaduke to capture the bridge. It took all day, but Marmaduke’s Division with support from Shelby’s Division crossed the Little Blue River and drove the Federals all the way through Independence and back to their main line of defense along the Big Blue River. That night Price’s army encamped in and around Independence. His wagon train of plunder and supplies contained hundreds of wagons. On October 22, Price planned to force a crossing of the Big Blue River at Byram’s Ford on the Independence to Westport Road.

By nightfall on October 22, the Confederate attack had succeeded. Curtis had fallen back to Westport and Kansas City, and Price now controlled Byram’s Ford. Price sent word back to the wagon train to start moving toward Byram’s Ford. Shortly after midnight, most of the wagons had crossed Byram’s Ford and were heading south down the Harrisonville Road toward the border town of New Santa Fe.

But late in the day on October 22, General Pleasonton’s cavalry reached In-dependence and attacked Price’s rearguard, driving them out of the town. With the wagon train safely away, the Confederate rearguard withdrew to the Big Blue River. Late that afternoon, a new cavalry brigade of 1,100 to 1,200 seasoned cavalry, commanded by Col. Edward F. Winslow, reached Independence, having come all the way from Memphis, Tennessee. Pleasonton ordered them for-ward, continuing the attack against the Confederate rearguard. Winslow led his men to within a few miles of Byram’s Ford and skirmished with the Confederate rearguard until about 10:30 p.m.


That night General Sterling Price devised a new plan for October 23. His wagon train was still in danger. And now he had two large enemy forces to deal with. So, with the wagon train lumbering south through the night, Price ordered Jo Shelby to attack the Federal army in Westport in the morning. To hold off the Federals now in Independence, Price ordered Marmaduke’s Division to man the defenses at Byram’s Ford and hold off Pleasonton while the wagon train lumbered away to safety.

Just that morning Federal troops had manned the defenses on the west side of the Big Blue River. On October 22, General Curtis had ordered the 4th Kansas State Militia down to Byram’s Ford to dig entrenchments and cut down trees to block the ford. But now the Confederates were dug in. To let their wagons through, the Confederates had cleared away downed trees blocking the ford and road. Now they were moving those obstacles back in place.


After their defeat on Saturday, Curtis had ordered his forces to fall back to Kansas City and Westport. The commanding general was concerned about his ability to protect Kansas from Price’s onslaught. At his headquarters in Kansas City on the Missouri River, he contemplated ordering all his forces to fall back within the Kansas City defenses. But General Blunt was not ready to go over to a defensive fight. After ensuring his troops were being resupplied, Blunt went to Kansas City to convince Curtis to attack in the morning. In the meantime, Curtis finally received word—Pleasonton was in Independence! Now Curtis’s thinking was aligned with Blunt. He ordered Blunt to prepare to move south, find the Confederates and attack.

Excited by their victory in the streets of Independence on Saturday, General Pleasonton was eager to press the attack in the morning; on October 23. From his headquarters in Independence, Pleasonton issued orders to renew the attack first thing in the morning. Pleasonton also ordered General McNeil south with his brigade to New Santa Fe to cut off the Confederate retreat. On Saturday morning, the Federals attacked the Confederate defenses at Byram’s Ford. It ended up taking all morning. Colonel Winslow took two brigades, crossed the river and launched an assault against the Confederates holding the high ground. Running low on ammunition, General Marmaduke ordered his men to withdraw south to catch up with the Confederate wagon train. Pleasonton took a short time to regroup and continued after the Confederates.

That same morning over in Westport, General Blunt moved south with three brigades crossing Brush Creek and moving up onto the plateau of present-day Loose Park. The Federals continue advancing south for another mile and ran into the troops from General Shelby’s division. The battle south of Westport had begun. Shelby’s troops pushed the Federals slowly north, until Blunt ordered his men to return to the north side of Brush Creek.

By this time, General Curtis had arrived at the front with reinforcements for Blunt. After regrouping, Blunt led his men across the creek again to engage the Confederates. Sometime that Sunday morning, a local farmer, George Thoman, showed up and demanded to see the commanding general. The result of this meeting was Thoman leading Curtis and a small force of Federal cavalry and artillery around to the undefended left flank of the Confederate forces. Just as Blunt was launching another attack against Shelby, Curtis ordered his artillery to open fire on Shelby’s left flank, throwing the Confederates into a state of confusion. Shelby shifted half of his command to deal with this new threat.

Around this time, two additional events added to Shelby’s dilemma. Pleasonton’s breakthrough at Byram’s Ford and Marmaduke’s withdrawal left General Fagan’s right flank exposed to an attack from Pleasonton. Fagan sent a request to Shelby for support. Shelby also received word from General Price that the wagon train was in danger. A brigade of Federal cavalry had arrived from the northeast and was preparing to attack the train. Price ordered Shelby to withdraw and come to the wagon train’s defense.

Shelby reacted by ordering Jackman’s Brigade to pull out and go to Fagan’s support. That left Shelby with only Thompson’s Brigade to hold off the three Federal brigades to his front. Colonel Jackman was able to slow down the Federal attack on the Confederate right, while Shelby proceeded to fall back south toward the wagon train. Now the Confederates were being pressed by the combined forces of Blunt and Pleasonton.


Leaving at midnight, General McNeil led his men slowly down the Santa Fe Trail, heading for New Santa Fe. As he was approaching the Harrisonville Road, McNeil saw the wagon train off in the distance, and it was guarded by thou-sands of Confederate cavalry. Thinking he was greatly outnumbered, McNeil hesitated to attack.

As it was, the train was being guarded by only one brigade commanded by Brig. Gen. William L. Cabell. There were thousands of mounted Confederates, but they were new recruits and they were unarmed. As soon as Cabell noticed the enemy cavalry, he dispatched a courier to notify Price. Then Cabell put his brigade in between the wagon train and the Federal threat. By the time McNeil decided to do something, Price had arrived and deployed the unarmed recruits into line of battle, hoping he could bluff the Federals. It worked, for all the cautious McNeil did was unlimber his artillery and do some long-range shelling of the Confederates. McNeil also sent forward a skirmish line, but eventually decided to fall back. The wagon train passed through New Santa Fe and continued south to safety.


While Thompson’s Brigade withdrew toward New Santa Fe, General Shelby joined Colonel Jackman as they made a fighting withdrawal south. About two miles south of where the morning fighting had taken place, the Confederate lined up behind a stone wall and prepared to hit the pursuing Federal forces with everything they had. Shelby only had one artillery piece left to support the small arms of his cavalry. When the Federals showed up, they were hit with canister and heavy small arms fire. The Federals took some losses and pulled back to regroup. Shelby made good his escape, withdrew through New Santa Fe and caught up with the wagon train. By early afternoon on Sunday, the fighting was over, and both sides were exhausted.

The Confederates bivouacked around 20 miles south near the headwaters of the Middle Fork of the Grand River. The Federal commanders met up to com-pare notes at a farmhouse near the intersection of present-day Bannister Road and Wornall Road. The Battle of Westport was over. The combined Federal army would pursue the retreating Confederates on Monday.

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