Battle of the Wilderness
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40 free Battle of the Wilderness trivia questions with answers — history quiz, new questions added Oct 2026.
The Battle of the Wilderness, fought in Virginia in May 1864, was the first time Ulysses S. Grant and Robert E. Lee faced each other in battle. Two armies groped through tangled second-growth woods where officers lost track of their own regiments, cavalry was nearly useless and cannon had little to shoot at. The stories that came out of it are some of the strangest of the Civil War. This quiz covers the fun facts people remember and the history behind them: the generals on both sides, the accidents and close calls, the things men said in the heat of the moment, the ground itself and the modern effort to preserve it. It is pitched for curious history fans rather than specialists. The opening questions are ones most Civil War readers can reason out, and the later ones reward anyone who has walked the field or read a history of the fighting.
30 of 40 questions with answers and explanations. Play the quiz
Q 01Which Confederate general's amputated arm lies buried at Ellwood Manor on the Wilderness battlefield?
Stonewall Jackson
Stonewall Jackson was shot by mistake by his own men a year before the battle, and his chaplain buried the arm in a family cemetery. A stone marker put up in 1903 still stands in the cemetery.
Q 02Which Confederate corps commander was shot by his own troops at the Battle of the Wilderness?
James Longstreet
James Longstreet was hit in the throat and shoulder by Virginians who mistook his mounted party for the enemy. He survived, but did not return to duty until that October.
Q 03What was the name of Robert E. Lee's horse, whose reins soldiers seized at the Battle of the Wilderness?
Traveller
Traveller was caught by the bridle when Lee began to follow a charge himself. The men would not go forward until their general moved somewhere safer.
Q 04What killed many wounded soldiers lying helpless between the lines at the Battle of the Wilderness?
Forest fires
Forest fires set by the gunfire spread through the dry undergrowth, and men on both sides were shocked to watch wounded comrades burn to death where they had fallen.
Q 05Which retail chain dropped plans for a store beside the Wilderness battlefield after a preservation fight?
Walmart
Walmart had county approval for a supercenter less than a quarter mile from the national park boundary. It withdrew in 2011, just as a lawsuit over the site was about to go to trial.
Q 06At the Wilderness, a brigade from which state halted its charge until Robert E. Lee rode back to safety?
Texas
Texas troops had just been cheered on by Lee, who waved his hat and then tried to ride in behind them. Of the 800 men who charged, only 250 came out unhurt.
Q 07Unable to see far in the smoke-filled Wilderness thickets, soldiers often aimed their shots at what?
Sounds
Sounds were often all a soldier had to aim at. That put attackers at a disadvantage, since they moved noisily through the brush toward defenders who stayed hidden.
Q 08Which Union cavalry general fought his West Point friend, Confederate Thomas Rosser, at the Wilderness?
George A. Custer
George A. Custer was attacked by Rosser on the Brock Road on the second morning. A six-gun battery arriving with another brigade turned the fight his way.
Q 09Which former Army of the Potomac commander led the separate IX Corps at the Battle of the Wilderness?
Ambrose Burnside
Ambrose Burnside outranked the army's commander, so his corps answered directly to Grant. His side-whiskers gave English the word sideburns.
Q 10Grant's march away from the Wilderness aimed to put his army between Lee and which city?
Richmond
Richmond was the prize Grant kept threatening. He hoped the move would force Lee to fight on open ground, where Union numbers and artillery could count.
Q 11Who kept formal command of the Army of the Potomac at the Wilderness while Grant travelled with it?
George Meade
George Meade, the victor of Gettysburg, kept the title while Grant rode alongside and set strategy. The arrangement left him chafing at the close supervision.
Q 12The Battle of the Wilderness was the opening fight of which 1864 Union drive through Virginia under Grant?
Overland Campaign
The Overland Campaign pushed Lee back into a siege at Petersburg by late June. After each battle Grant sidestepped to the southeast and came on again.
Q 13The Wilderness was fought in the same Virginia thickets as which Confederate victory of a year earlier?
Chancellorsville
Q 21Which VI Corps commander, nearly captured at the Wilderness, was killed by a sharpshooter three days later?
John Sedgwick
John Sedgwick escaped a dusk flank attack in which two of his brigadiers were taken prisoner. On May 9 he was shot moments after joking that the enemy could not hit an elephant at that range.
Q 22What hidden route let Confederate brigades slip around Winfield Hancock's flank at the Wilderness?
An unfinished railroad
An unfinished railroad bed ran through the woods south of the Plank Road. Lee's chief engineer explored it that morning and found it led straight to the unguarded Union left.
Q 23Winfield Hancock said a flank attack at the Wilderness rolled up his line like which everyday object?
Chancellorsville saw Lee beat an army more than twice the size of his own. That win is why he was glad to catch Grant on the same tangled ground.
Q 14Which Virginia river, the winter dividing line between the armies, did Grant cross to enter the Wilderness?
Rapidan
Rapidan fords took the troops over on May 4, and behind them rolled a supply train of some 4,300 wagons that stretched for 60 to 70 miles.
Q 15Which battle began the day after the Wilderness, when Lee beat Grant to a crossroads ten miles southeast?
Spotsylvania
Spotsylvania became a two-week struggle because Lee guessed where Grant was heading. His men got there first and dug formidable earthworks.
Q 16Which Confederate cavalry chief at the Wilderness was mortally wounded at Yellow Tavern only days later?
Jeb Stuart
Jeb Stuart was shot on May 11 as retreating Michigan horsemen streamed past him, and he died the next day. His troopers had been scattered across the region when the campaign opened.
Q 17Which general did Grant bring east from an infantry command to lead the Union cavalry at the Wilderness?
Philip Sheridan
Philip Sheridan was new to the job, and the dense woods left his horsemen little room to fight. Most of the cavalry clashes took place on the roads south of the infantry.
Q 18How do historians and the National Park Service usually sum up the result of the Battle of the Wilderness?
Inconclusive
Inconclusive is the usual verdict because neither army was driven from the field. Lee fought Grant to a standoff, yet Grant marched on south instead of retreating.
Q 19Before the Wilderness, Grant was promoted to which rank, first held in the U.S. Army by George Washington?
Lieutenant general
Lieutenant general was revived by Congress in February 1864 so that Lincoln could place Grant over every Union army. The promotion came with command of them all.
Q 20The Wilderness battlefield lies about 20 miles west of which Virginia city, scene of a Union defeat in 1862?
Fredericksburg
Fredericksburg lends its name to the national military park that now protects parts of four battlefields, the Wilderness the westernmost of them.
A wet blanket
A wet blanket was Hancock's image for how his left wing folded when the attack hit at 11 a.m. He rallied the men in trenches along the Brock Road and held there for the rest of the day.
Q 24Grant mocked officers at the Wilderness for fearing Lee would suddenly pull off which acrobatic move?
A double somersault
A double somersault, Grant snapped, would have to land Lee in the Union rear and on both flanks at once. He told the worried officer to think about what they were going to do instead.
Q 25Which Union general called Grant's choice to press on after the Wilderness the grandest act of his life?
William T. Sherman
William T. Sherman, who was about to strike into Georgia on Grant's orders, added that he now felt the rebellion would be crushed.
Q 26Which V Corps commander, the hero of Little Round Top, opened the Battle of the Wilderness on the Orange Turnpike?
Gouverneur Warren
Gouverneur Warren asked to wait for support on his right, but his impatient superiors ordered him in at once. The attack was thrown back across the clearing it had crossed.
Q 27Which Confederate general, who had lost a leg in 1862, led the Second Corps at the Wilderness?
Richard Ewell
Richard Ewell reached the western edge of a clearing first and had his men dig in. Lee had told him not to advance too fast, because the rest of the army was still out of reach.
Q 28Which wealthy New York landowner, a Union division commander, was mortally wounded at the Wilderness?
James Wadsworth
James Wadsworth was 56, the oldest division commander in the army by about nine years. Shot in the head on the second day, he died in a Confederate field hospital.
Q 29Which future Georgia governor led the Confederate dusk attack on the Union right at the Wilderness?
John B. Gordon
John B. Gordon had scouted the exposed flank that morning, but his division commander thought the attack too risky. It was not approved until about 5:30 p.m., with little daylight left.
Q 30The Wilderness thickets grew up after the region's old trees were cut to make charcoal for what?
Iron furnaces
Iron furnaces in the region ate up the timber in the early 1800s. What grew back was a tangle of briars, pine, cedar and low-branched hardwoods that an army could barely see through.