As the Union Army now under the watchful eye of Lieutenant General Ulysses S. Grant marched southeast, the Army of Northern Virginia moved to intercept them. Union artillery and their sheer numbers of men could greatly threaten General Lee's much smaller force which was still separated from General Longstreet's Corps. Officers at the regimental, brigade, and division level who had received promotions after the catastrophic casualties of Gettysburg would receive their first test with large scale battle and numerous casualties with their new commands. Without Longstreet's Corps, the Butternuts could perhaps even the odds through audacious tactics and by challenging their Northern foes, not on open ground, but in the twisted mire of underbrush and trees known locally as the Wilderness (see photograph below). However, not one to rush into battle foolishly, General Lee made clear to his Corps commanders, as General Ewell would report, that "he preferred not to bring on a general engagement before General Longstreet came up."

Much had changed for the Union army as well since their victory at Gettysburg. In September of 1863, the 11th and 12th Corps transferred west to aid Major General William Rosecrans' efforts to defeat General Braxton Bragg. The remnants of the devastated 1st Corps, the former command of the deceased Major General John Fulton Reynolds, ceased to exist after being folded into the Potomac Army's 5th Corps. Likewise, the 3rd Corps which suffered huge losses on July 2, 1863, merged with both the 2nd and 6th Corps. [9] Major Generals Winfield Scott Hancock and the beloved "Uncle" John Sedgwick still held command of the 2nd and 6th Corps respectively. Major General Gouverneur Kemble Warren, the hero of Little Round Top, now commanded the men of the 5th Corps.

Warren's 5th Corps moved east along the Germanna Plank Road, heading towards the old Chancellorsville Battlefield and the ghosts of horrific battles past. Before clearing the dense ocean of underbrush, they encountered Confederate Lt. General Richard Stoddert Ewell's Corps near the Elwood Manor where the Reverend Beverley Tucker Lacy had buried Stonewall Jackson's amputated arm lost during his evening recognizance almost one year earlier to the day. General Warren would speak of their initial success and then repulse on this first day of the Battle of the Wilderness. "The attack failed because Wright's division, of the Sixth Corps, was unable on account of the woods to get up on our right flank and meet the division (Johnson's) that flanked us. Wright became engaged sometime afterward. We lost heavily in this attack, and the thick woods caused much confusion in our lines." During this time, as Warren continued, "General Hancock was ordered up from Todd's Tavern (south of the emerging battlefield), and also engaged Hill's corps."

General Hancock had been ordered "to endeavor to connect with General Warren on the Orange Plank Road" but experienced difficulty in maneuvering due again to the thickly tangled forbidding woods. Hancock stated of these obstacles, "Owing to the fact of the Brock road being very narrow and heavily wooded on both sides, the formation of the infantry in line of battle was extremely slow." The Chewning Farm, pictured below, remained for part of the day unoccupied and sat squarely in the middle of the conflict between Ewell and Warren to the west of the farm and that of Powell Hill and Hancock just to the east. The Union's 2nd Corps commander would offer of this day, "The battle raged with great severity and obstinacy until about 8 p.m. without decided advantage to either party." And so the horrendous casualty counts of the 1864 Overland Campaign would begin. [5]

General Lee's Official Report would very briefly discuss the events of this ominous beginning to months of conflict. "The enemy crossed the Rapidan yesterday at Ely's and Germanna Fords. Two corps of this army moved to oppose him Ewell's, by the old turnpike, and Hill's, by the plank road. They arrived this morning in close proximity to the enemy's line of march. A strong attack was made upon Ewell, who repulsed it, capturing many prisoners and four pieces of artillery. The enemy subsequently concentrated upon General Hill, who, with Heth's and Wilcox's divisions, successfully resisted repeated and desperate assaults. A large force of cavalry and artillery on our right flank was driven back by Rosser's brigade. By the blessing of God we maintained our position against every effort until night, when the contest closed. We have to mourn the loss of many brave officers and men. The gallant Brig. Gen. J. M. Jones was killed, and Brig. Gen. L. A. Stafford, I fear, mortally wounded while leading his command with conspicuous valor." [5]

General Grant would, in his eloquently written memoirs, offer justification of a kind for his approach to the coming battles which would cost both sides tens of thousands of men. He begins his discussion of the Battle of the Wilderness by offering, "Soon after midnight, May 3d–4th, the Army of the Potomac moved out from its position north Rapidan, to start upon that memorable campaign, destined to result in the capture of the Confederate capital and the army defending it. This was not to be accomplished, however, without as desperate fighting as the world has ever witnessed; not to be consummated in a day, a week, a month, single season. The losses inflicted, and endured, were destined to be severe; but the armies now confronting each other had already been in deadly conflict for a period of three years, with immense losses in killed, by death from sickness, captured and wounded; and neither had made any real progress accomplishing the final end. [46]