The Federals plodded southward on the 19th over roads that were fast becoming quagmires. That evening they reached Pontotoc, where they halted only long enough to destroy government property and sift through captured documents abandoned by a retreating militia company. They went into camp about five miles south of Pontotoc. Despite the deteriorating roads, the hard-riding horsemen were maintaining a brisk pace of 30 miles per day.

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To help keep up that pace, Grierson stripped his command of dead weight. In a midnight inspection he personally weeded out 175 of the least effective troopers. At 3:00 a.m. on April 20, Major Hiram Love of the 2d Iowa led this Quinine Brigade–along with prisoners, broken down horses, and a single artillery piece–out of the Federal camp toward La Grange. By moving in columns of fours under cover of darkness, Grierson hoped Love would deceive local residents into thinking the entire command had turned back.

With Love on his way north, the main column resumed its march. The force encamped shortly after dark on the 20th. In four days the raiders had encountered only token resistance, but Barteau’s Confederate cavalry was fast closing in. They had entered Pontotoc well behind the Federal force on the morning of the 20th, but closed the gap with hard riding that night. By daybreak on the 21st they were scant hours behind the Union horsemen.

Grierson did not know how close his pursuers were, but he certainly expected pursuit. To obscure his trail, he detached Hatch’s 500-man 2d Iowa–nearly a third of his command–and a gun from Smith’s battery. Hatch, a bombastic 31-year-old former lumberman, left the main column with instructions to strike the Mobile & Ohio Railroad near West Point, destroying its tracks as far south as Macon, about halfway between West Point and Meridian. He was then to swing through Alabama, doing further damage to rail and telegraph lines during his return to La Grange.

Before joining Hatch’s detachment, Company E of his 2d Iowa and the two-pounder artillery piece followed the main column three or four miles toward Starkville. There the Iowans wheeled about and returned in columns of fours, obliterating hoofprints in the opposite direction. They turned the tiny cannon at four different spots in the road to leave distinct sets of wheel impressions, suggesting that four different cannon had turned. With a little luck, pursuing Confederates would pick up the freshest tracks in the thick mud and conclude that Grierson’s entire force had turned east toward the Mobile & Ohio.

Hatch’s diversion worked flawlessly. Barteau, arriving at the junction shortly before noon, reported, My advance guard fired upon a party of 20 of the enemy, supposed to be the rear guard. This party fled and took the Starkville road. The enemy had divided, 200 going to Starkville and 700 continuing their march on the West Point road. Barteau turned eastward in pursuit.

At 2:00 p.m. Barteau fell upon the Iowans’ flanks and rear two miles northwest of Palo Alto. After a fierce skirmish, the Confederates withdrew. Their position, however, covered the road leading south to West Point and Macon, compelling Hatch to reevaluate his orders. He believed it was important to divert the enemy’s cavalry from Colonel Grierson, so his Hawkeyes began a slow withdrawal northward, drawing the pursuing Rebels along with them. Barteau would finally break off contact on the 24th.

Meanwhile, the 950 troopers of the 6th and 7th Illinois and Smith’s four remaining guns raced southward. Shortly after noon on the 21st, a half-dozen horsemen at the head of the column shed their Union blue in favor of civilian garb. Each cradled a shotgun or long rifle. The brainchild of Lieutenant Colonel William D. Blackburn of the 7th and commanded by Quartermaster Sergeant Richard W. Surby, this unit of Butternut Guerrillas would serve as the eyes and ears of the Yankee raiders.

The next day Grierson again focused his attention on the Mobile & Ohio Railroad that paralleled his line of march 25 miles to the east. Uncertain of Hatch’s fate, he dispatched Captain Henry C. Forbes and 35 men of the 7th’s Company B to disrupt the tracks at Macon.

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