Portrait of Ulysses S. Grant

The Battle of Fair Oaks and Darbytown Road was Ulysses S. Grant’s last Union attempt to threaten Richmond during 1864. [Wikimedia Commons]

Battle of Fair Oaks and Darbytown Road

October 27–28, 1864

Fought from October 27 - 28, 1864, during the Petersburg Campaign, the Battle of Fair Oaks and Darbytown Road, also known as the Second Battle of Fair Oaks, was the last failed Union attempt to capture Richmond, Virginia in 1864.

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Prelude to the Battle

Grant in Charge

On March 10, 1864, President Abraham Lincoln appointed Ulysses S. Grant as General-in-Chief of the Armies of the United States. Grant brought with him, from his successes in the Western Theater of the war, a reputation for the doggedness that Lincoln was seeking in his generals. Unlike other Union generals, Grant was tenacious.

Grant Focuses on Lee

Upon his arrival in Washington, Grant drafted a plan to get the various Union armies in the field to act in concert. He also devised his Overland Campaign to invade east-central Virginia. Unlike previous campaigns into that area, Grant’s plan focused upon defeating General Robert E. Lee and his Army of Northern Virginia rather than capturing or occupying geographic locations. Grant instructed Major General George G. Meade, who commanded the Army of the Potomac, “Wherever Lee goes, there you will go also.” Grant realized that, with the superior resources he had at his disposal, Lee would lose a war of attrition, as long as Northern troops persistently engaged the Confederates.

Overland Campaign

On May 4, 1864, Grant launched his Overland Campaign when the Army of the Potomac crossed the Rappahannock and Rapidan Rivers, occupying an area locally known as the Wilderness. For the next eight weeks, the two sides engaged in a series of horrific battles that produced unprecedented numbers of casualties. Following a bloody frontal assault at Cold Harbor that cost the Federals roughly 13,000 casualties, Grant abandoned his hope to defeat Lee’s army head-on. Instead, Grant aimed to isolate the Army of Northern Virginia at Richmond and slowly starve it into submission by cutting off its supply lines. The key to the plan was capturing Petersburg, Virginia.

Petersburg Geography

Petersburg, Virginia, sits on the south bank of the Appomattox River, approximately twenty miles south of Richmond. During the Civil War, the Richmond and Petersburg Railroad was an important conduit for supplies to the Confederate capital. Besides the Richmond and Petersburg Railroad, two other rail lines converged at Petersburg. The Weldon Railroad (also called the Petersburg and Weldon Railroad) connected Petersburg to the Confederacy’s last linkage to overseas markets at Wilmington, North Carolina. Farther to the west, the South Side Railroad joined Petersburg to Lynchburg, Virginia, and points westward. If Grant could cut the rail lines, it would force Lee to abandon Richmond.

Action East of Richmond

Although Grant’s focus during the summer and fall of 1864 was on cutting off supply routes into Petersburg, he also launched several assaults north of the James River against Richmond. Grant recognized that forcing Lee to defend two fronts would thin the Confederate defenses around Petersburg, enhancing Union expectations for success. Most of the action on the outskirts of Richmond during the summer centered on Darbytown and New Market Roads, which ran roughly parallel to each other into the Confederate capital from the southeast.

At the Battle of Chaffin’s Farm and New Market Heights (September 29–30, 1864) Union soldiers captured Fort Harrison and other portions of Richmond’s outer defenses along Darbytown and New Market Roads. A week later, at the Battle of Darbytown and New Market Roads (October 7, 1864), Federals forced Lee’s soldiers to retreat to Richmond’s inner defenses. On October 11, Lee ordered the construction of new breastworks outside of Richmond’s inner defenses. At the Battle of Darbytown Road (October 13, 1864), Union forces failed to prevent the Rebels from completing their new fortifications.

Two-pronged Attack Plan

On October 27, 1864, Grant launched another two-pronged offensive against Petersburg and Richmond. While Major General Winfield Scott Hancock’s Union forces south of Petersburg attempted to secure the Boydton Plank Road, Major General Benjamin Butler and the Army of the James once again attacked the Richmond defenses around Darbytown Road. Grant intended Butler’s assault to serve as a diversion for Hancock’s offensive, but Butler had aspirations of capturing the Confederate capital.

Butler’s Mission

Butler’s plan called for Major General Alfred Terry’s 10th Corps to demonstrate as far north as the Charles City Road. Meanwhile, Major General Godfrey Weitzel’s 18th Corps would follow Major General August Kautz’s cavalry division around Terry’s right and move west over the Williamsburg Road to attack the left flank of the Confederate defenses near Fair Oaks. If the Federals could turn the Rebel line, Butler believed that Kautz’s cavalry, followed by Weitzel’s infantry, could proceed west on the Williamsburg Road and storm the Confederate capital.

The mission began at approximately 4:30 a.m. on October 27, when Terry’s soldiers left their entrenchments near New Market Road and moved north over the same ground that they had covered during the Battle of Darbytown Road two weeks earlier. As planned, Terry advanced to the Charles City Road (which ran roughly parallel to the Darbytown and New Market Roads) and halted.

Confederates Reinforce

Confusion between Kautz and Weitzel delayed the arrival of the 18th Corps at the Williamsburg Road until 1 p.m. Weitzel then spent the next two hours scouting and positioning his troops. By that time, General James Longstreet, who had recently assumed command of the Confederate defenses at Richmond, surmised Weitzel’s intentions and shifted Major General Charles W. Field’s division to reinforce his left flank.

Federals Withdraw

At approximately 3:30 p.m., Weitzel finally launched his assault by sending only two of his seven brigades forward across three hundred yards of open ground. The Confederate defenders greeted the Yankees with a hail of musket and artillery fire that sent their adversaries fleeing. Weitzel quickly withdrew. Later, under the cover of darkness, he and Terry returned to the main Union lines at New Market Road.

Aftermath of the Battle

In his after-action summary, Longstreet reported that

The fruits of these successes, so creditable to the officers and men engaged, and resulting in the complete defeat of a most determined effort to take Richmond on the north side, amounted to (11) eleven stands of colors, captured in the assault of Field’s position, and about (600) six hundred prisoners. . . .

The Battle of Fair Oaks and Darbytown Road was the last failed Union attempt to threaten Richmond during 1864. The Rebel victory cost the Union over 1,700 casualties compared to only 100 for the Confederacy.

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Citation Information

The following information is provided for citations.

  • Article Title Battle of Fair Oaks and Darbytown Road
  • Coverage October 27–28, 1864
  • Author
  • Keywords Battle of Fair Oaks and Darbytown Road
  • Website Name American History Central
  • Access Date August 1, 2021
  • Publisher R.Squared Communications, LLC
  • Original Published Date
  • Date of Last Update March 19, 2021
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