Civil War Service
Upon his return to the United States, he was elected as a delegate to North Carolina's secession convention. He resigned from the commission after the passage of the Ordinance of Secession and joined the Confederate Army as the major of the newly formed 4th North Carolina Infantry on May 16, 1861. He saw his first combat action at the First Battle of Bull Run in Virginia on July 21. Grimes was promoted to lieutenant colonel on May 1, 1862, and fought at the Battle of Seven Pines, during which he was wounded when his injured horse fell on top of him on May 31. On June 19, 1862, Grimes was promoted to the rank of colonel and given command of the 4th North Carolina Infantry, now part of the Army of Northern Virginia. Grimes led the regiment during the Peninsula Campaign, but missed the Maryland Campaign and the Battle of Antietam due to a severe leg injury incurred when his horse kicked him on September 5 near Edward's Ferry in Maryland. Upon recovery Grimes returned to field duty in temporary command of an infantry brigade within the division of Maj. Gen. Daniel Harvey Hill. He fought with the rest of Stonewall Jackson's Second Corps at the Battle of Fredericksburg that December, where his men repelled a Union attack.
Grimes returned to his regimental command before the 1863 Chancellorsville Campaign, where he was wounded again, this time in a foot, on May 3. During the first day's fighting at Gettysburg, Grimes' regiment was the first organized Confederate unit to enter the streets of Gettysburg, Pennsylvania. He was in charge of the rear guard during a part of the army's retreat into Virginia following the three-day battle. On September 15, 1863, he married Charlotte Emily Bryan, and they eventually had ten children together, including John Bryan Grimes, who would become North Carolina's secretary of state. Again, another son named Bryan Grimes died in childhood.
During the 1864 Overland Campaign, Grimes was promoted to the rank of brigadier general on May 19, and given permanent command of his brigade of North Carolinians. That autumn, he fought in the Shenandoah Valley Campaign as part of the army of Lt. Gen. Jubal A. Early. When Maj. Gen. Stephen D. Ramseur was killed at Cedar Creek, Grimes assumed command of his division on December 9 and led it for the rest of the war. On October 19 while at Cedar Creek he was wounded in a leg.
On February 15, 1865, Grimes was promoted to major general, the last man appointed to that rank in the Army of Northern Virginia. He served in the trenches surrounding Petersburg and joined Robert E. Lee's retreat to the west that ended when the way was blocked by Federal columns near Appomattox Court House. Grimes led an attack that temporarily cleared Federals from the Lynchburg Road, briefly opening up a possible route of escape for a portion of Lee's army. However, Lee chose to surrender instead of risking useless further bloodshed.
Following the Appomattox Campaign, Grimes surrendered along with the rest of the Army of Northern Virginia on April 9, 1865, and was paroled at Appomattox Court House. He was pardonned by the U.S. government on June 26, 1866.
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“He was high and mighty. But the kindest creature to his slaves—and the unfortunate results of his bad ways were not sold, had not to jump over ice blocks. They were kept in full view and provided for handsomely in his will. His wife and daughters in the might of their purity and innocence are supposed never to dream of what is as plain before their eyes as the sunlight, and they play their parts of unsuspecting angels to the letter.”
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