Battle of Chickasaw Bayou The Battle of Chickasaw Bayou , also called the Battle of Walnut Hills , fought December 26 – 29 , 1862 , was the opening engagement of the Vicksburg Campaign during the American Civil War . Confederate forces under Lt . Gen . John C . Pemberton repulsed an advance by Union Maj . Gen . William T . Sherman that was intended to lead to the capture of Vicksburg , Mississippi . On December 26 , three Union divisions under Sherman disembarked at Johnson ' s Plantation on the Yazoo River to approach the Vicksburg defenses from the northeast while a fourth landed farther upstream on December 27 . On December 27 , the Federals pushed their lines forward through the swamps toward the Walnut Hills , which were strongly defended . On December 28 , several futile attempts were made to get around these defenses . On December 29 , Sherman ordered a frontal assault , which was repulsed with heavy casualties , and then withdrew . This Confederate victory frustrated Maj . Gen . Ulysses S . Grant ' s attempts to take Vicksburg by a direct approach . Background and opposing forces . Starting in November 1862 , Maj . Gen . Ulysses S . Grant , commanding Union forces in Mississippi , undertook a campaign to capture the city of Vicksburg , high on the bluffs of the Mississippi River , one of two Confederate strong points ( the other being Port Hudson , Louisiana ) that denied the Union complete control of the Mississippi River . Grant split his 70 , 000 - man army into two wings — one commanded by himself and one commanded by Maj . Gen . William T . Sherman . Sherman commanded the Right Wing , or XIII Corps , Army of the Tennessee , redesignated the XV Corps on December 22 . His expeditionary force of 32 , 000 troops was organized into four divisions , commanded by Brig . Gens . Andrew J . Smith , Morgan L . Smith , George W . Morgan , and Frederick Steele . Grant ' s wing marched south down the Mississippi Central Railroad , making a forward base at Holly Springs . He planned a two - pronged assault in the direction of Vicksburg . As Sherman advanced down the river , Grant would continue with the remaining forces ( about 40 , 000 ) down the railroad line to Oxford , where he would wait for developments , hoping to lure the Confederate army out of the city to attack him in the vicinity of Grenada , Mississippi . The seven gunboats and fifty - nine troop transports commanded by Rear Adm . David D . Porter departed Memphis , Tennessee , on December 20 , stopped at Helena , Arkansas , to pick up additional troops , and arrived at Milliken ' s Bend above Vicksburg on December 24 . After advancing up the Yazoo River , the transports disembarked Sherman ' s men at Johnson ' s Plantation , opposite Steele ' s Bayou , north of the city . ( Preceding the landing , the U . S . Navy conducted torpedo clearing operations on the Yazoo , during which the ironclad USS " Cairo " was sunk . ) The Confederate forces opposing Sherman ' s advance were from the Department of Mississippi and East Louisiana , commanded by Lt . Gen . John C . Pemberton , a Pennsylvanian who chose to fight for the South . The officer in direct command of the defenses of Vicksburg was Maj . Gen . Martin L . Smith , who commanded four brigades led by Brig . Gens . Seth M . Barton , John C . Vaughn , John Gregg , and Edward D . Tracy . Brig . Gen . Stephen D . Lee commanded a provisional division with brigades commanded by Cols . William T . Withers and Allen Thomas ; Lee was the primary commander of the Confederate defense in the Walnut Hills until the arrival late on December 29 of Maj . Gen . Carter L . Stevenson . Although the Union forces outnumbered the men to their front by two to one ( 30 , 720 to 13 , 792 ) , they faced a formidable maze of both natural and man - made defenses . First was a thick entanglement of trees , which was broken intermittently by swampland . Chickasaw Bayou , a stream that was chest - deep , 50 yards wide , and choked with trees , also acted as a potential barrier to Sherman ' s men because it was parallel to the planned line of advance and could interrupt communication between units . Furthermore , the Confederates had formed dense barriers using felled trees for abatis . Battle . On December 26 , Sherman deployed the brigades of Col . John F . DeCourcy and Brig . Gens . David Stuart and Francis P . Blair , Jr . , to perform reconnaissance and find weaknesses in a Confederate defense . They moved slowly ahead through the difficult terrain , skirmishing with S . D . Lee ' s covering force that had been at Mrs . Lake ' s plantation . On December 28 , Steele ' s division attempted to turn the Confederate right flank , but was repulsed by Confederate artillery fire as they advanced on a narrow front . On the morning of December 29 , Sherman ordered an artillery bombardment of the Confederate defenses to weaken them before a general Federal advance . For almost four hours , an artillery duel took place all along the line of battle , but did little damage . At 11 a . m . , the duel ceased , and the infantry deployed into their lines of battle . Understanding the formidable nature of the Confederate fortifications , Sherman remarked , " We will lose 5 , 000 men before we take Vicksburg , and may as well lose them here as anywhere else . " At noon , Union troops advanced with a cheer . Blair ' s brigade moved on the left , DeCourcy ' s in the center , followed by Brig . Gen . John M . Thayer ' s brigade on the right ; Thayer ' s brigade lost its way and only one regiment , the 4th Iowa Infantry , was engaged . Colonel James A . Williamson , commanding the 4th Iowa , was later awarded the Medal of Honor for his actions that day . They crossed water barriers and abatis and carried the advance rifle pits on the weight of sheer numbers , but met stiff resistance when they came against the main Confederate line and began to crumble under the heavy fire . The survivors fell back across the bayou on a corduroy bridge . S . D . Lee ordered his men to make a counterattack , during which they captured 332 Federals and four battle flags . Another assault ordered by Sherman was conducted by two divisions under A . J . Smith ( his own division and that of M . L . Smith , who had been wounded the day before ) advancing across Chickasaw Bayou to seize the Indian Mound that was in the center of the Confederate line , defended by Barton and Gregg . Skirmishers from the brigades of Cols . Giles A . Smith and Thomas Kilby Smith covered the bayou crossing and the 6th Missouri Infantry of G . A . Smith ' s brigade led the way with 20 pioneers , building a road on the far bank . Five attempts to carry the position at the Indian mound were repulsed . On the far Union right , an attack by Col . William J . Landram ' s brigade of A . J . Smith ' s division was easily repulsed by the Confederates of Vaughn ' s brigade . Aftermath . That evening , Sherman declared that he was " generally satisfied with the high spirit manifested " by his men although their attacks had failed in the face of strong Confederate positions on the high bluffs . Union casualties were 208 killed , 1 , 005 wounded , and 563 captured or missing ; Confederate casualties were 63 killed , 134 wounded , 10 missing . Sherman conferred with Adm . Porter , whose naval gunfire had also failed to do any significant damage to the enemy . They decided to resume the attacks on the following day and Porter sent a boat to Memphis to get more small arms ammunition . By the morning of December 30 , Sherman had concluded that resuming the attacks at the same location would be fruitless and he and Porter planned a joint army - navy attack on Drumgould ' s Bluff to the northeast , hoping that the steep bluffs would provide cover for his men as they advanced . It was imperative that such a movement be started in secrecy so that the Confederates would not shift their defensive forces . The movement commenced on December 31 , but was called off in heavy fog on January 1 , 1863 . During this period , the overland half of Grant ' s offensive was also failing . His lines of communication were disrupted by raids by Brig . Gen . Nathan Bedford Forrest and by Maj . Gen . Earl Van Dorn , who destroyed the large supply depot at Holly Springs . Unable to sustain his army without these supplies , Grant abandoned his overland advance . Sherman realized that his corps would not be reinforced by Grant and decided to withdraw his expedition , moving to the mouth of the Yazoo on January 2 . On January 5 , Sherman sent a letter to General - in - Chief Henry W . Halleck , summing up the campaign ( in a manner reminiscent of a famous statement by Julius Caesar ) , " I reached Vicksburg at the time appointed , landed , assaulted , and failed . " He and his command were then temporarily assigned to Maj . Gen . John A . McClernand for an expedition up the Arkansas River and the Battle of Arkansas Post . Although Grant tried a number of operations , or " experiments " , to reach Vicksburg over the winter , the Vicksburg Campaign did not begin again in earnest until April 1863 .