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After Grant's army escaped from the trap that Lee had set for it at the Battle of North Anna, it began to move again around the right flank of Lee's army, in a continuation of the maneuvering that had characterized the campaign throughout May 1864. Lee gave orders for his army to fall back 12 miles to Atlee's Station, only 9 miles north of the Confederate capital of Richmond, and near the site of the start of the Seven Days Battles of 1862.
On May 27, Union cavalry established a bridgehead on the south side of the Pamunkey River, near the Hanovertown Ford. Brig. Gen. George A. Custer's Michigan cavalry brigade (from the division of Maj. Gen. Alfred T.A. Torbert in Maj. Gen. Philip Sheridan's Cavalry Corps of the Army of the Potomac) scattered the mounted Confederate pickets guarding the ford and an engineer regiment constructed a pontoon bridge. The rest of Torbert's division then crossed the river, followed by the cavalry division of Maj. Gen. David McM. Gregg and a division of Union infantry.
Lee knew that his best defensive position against Grant would be the low ridge on the southern bank of Totopotomoy Creek, but he was not certain of Grant's specific plans; if Grant was not intending to cross the Pamunkey in force at Hanovertown, the Union army could outflank him and head directly to Richmond. Lee ordered cavalry under Maj. Gen. Wade Hampton to make a reconnaissance in force, break through the Union cavalry screen, and find the Union infantry.
On May 28, Hampton rode off with three veteran cavalry brigades, a battery of horse artillery, and three regiments of mounted infantry, green troops from South Carolina. As more of Grant's troops crossed the pontoon bridge over the Pamunkey, Gregg led his Union cavalry division probing west from Hanovertown, searching for Lee. (Torbert's division began to picket along Crump's Creek in the direction of Hanover Courthouse.) Three miles west of Hanovertown, and a mile beyond a large blacksmith shop called Haw's Shop, Gregg's troopers ran into Hampton at Enon Church, finding the Confederate cavalrymen dismounted in a wooden area behind a swamp, hurriedly erecting breastworks made of logs and rails, and well covered by artillery. Brig. Gen. Henry E. Davies, Jr., of Gregg's division deployed pickets from the 10th New York Cavalry to Hampton's front. Hampton reportedly exclaimed, "We've got the Yankees where we want them now." It was impossible to turn the position, due to a stream to the north and a mill pond to the south, so Gregg, despite being outnumbered, launched a frontal assault.
The Confederates met the Union charge with a wall of fire. The South Carolina mounted infantry carried Enfield rifles, which outranged the carbines carried by the Federal cavalry, killing or wounding 256. As Davies rode into the fighting, his saber was cut in half by a Minié ball and his horse's tail was shot off. Union return fire was heavy as well, because the troopers were armed with seven-shot Spencer repeating carbines. One Pennsylvania trooper estimated that the 200 men in his unit fired 18,000 rounds. Their carbines got so hot that from time to time the men had to pause to let them cool.
As Gregg's first attack ground to a halt, and his second brigade attack under J. Irvin Gregg failed to dislodge the Confederates, Hampton's men moved out from their works and started a series of counterattacks. Gregg sent for reinforcements from Sheridan, who released two brigades from Torbert's division. (There was plenty of infantry nearby, but Maj. Gen. George G. Meade refused Sheridan's request for two brigades.) Torbert's brigade under Brig. Gen. Wesley Merritt extended Greg's line to the right, thwarting Hampton's attempted flanking maneuver. Sheridan also threw Custer's brigade into the fight. He pointed toward the Confederates and commanded, "Custer, I want you to go in and give those fellows hell!"
Due to the heavily wooded terrain, Custer had his brigade dismount and deploy in a long, double-ranked line of battle, as if they were infantrymen. However, Custer inspired his men by staying mounted as he led them forward, waving his hat in full view of the enemy. Some of the relatively inexperienced South Carolina infantry mistook a Union shift in position for a retreat and charged after them, only to run into Custer's men, who captured 80 of the Confederates. Forty one of the Union cavalrymen fell in the attack, as did Custer's horse, but their enthusiastic charge caused Hampton's men to withdraw. (Another factor was that Hampton had just received intelligence from prisoners on the location of two Union corps, which meant that his reconnaissance mission had been successfully completed.)
The Battle of Haw's Shop lasted for over seven hours and was the bloodiest cavalry battle since Brandy Station in 1863. Union casualties were 256 men in Gregg's division and another 41 from Custer's brigade, including Private John Huff, the cavalryman from the 5th Michigan who had fatally shot J.E.B. Stuart at Yellow Tavern. Confederate losses were never tabulated officially, but Union reports claimed they buried 187 enemy bodies after the battle, recovered 40 to 50 wounded men, and captured 80 South Carolinians. Gregg paid tribute to the Confederates "who resisted with courage and desperation unsurpassed." He later wrote that the battle "has always been regarded by the Second Division as one of its severest."
Since the Confederates withdrew, the battle was a technical Union victory, but at a high cost. Hampton had delayed the Union advance for seven hours and General Lee received the valuable intelligence he had sought. This information caused him to shift the Army of Northern Virginia to a new blocking position at Cold Harbor.