The Monroe Guard had been organized in 1859 by John Echols following John Brown’s raid at Harper’s Ferry when they were known as part of the Rockbridge Militia company. The 108 members of the company came from Monroe County, Virginia (now West Virginia) and they left Union, the county seat, on May 13, 1861 under the command of Captain Hugh Tiffany. Company D joined six other companies at Harper’s Ferry to form the 27th Virginia Infantry Regiment. Command of the regiment fell upon Lt. Col. John Echols of Company D. The 27th was attached to the First Virginia Brigade with the 2nd Va, 4th VA, 5th VA, and 33rd VA under the command of Colonel Thomas Jonathan Jackson.

     The 27th’s first major action of the war was at First Manassas where it earned the nickname "the Bloody 27th" because of its initial losses. It was also here that the brigade and Jackson received the moniker "Stonewall" for the stand the brigade made at the Henry Hill house late in the battle. It would become the only official nickname recognized by the Confederate government for a Confederate unit. Captain Tiffany became the first member of the Company to die in the war as he led the regiment forward at Manassas.

     The entire Stonewall Brigade earned its reputation in both armies during the Valley Campaign of 1862, marching 670 miles in 35 days, fighting five major battles and defeating three separate Union armies totaling four times their own strength, earning the name "foot cavalry". In one 48 hour period, the brigade marched 50 miles, fought in and won the First Battle of Winchester.

     The regiment lost its commander, Major Elisha Paxton as well as its original commander, Stonewall Jackson at Chancellorsville in May 1863. Many in the brigade petitioned General Lee to help bear Jackson’s body back to Lexington but because of the military situation, Lee had to decline.

     The regiment was virtually wiped out in 1864 at the battle of Spotsylvania when damp weather soaked their powder and the Union Second Corps under Winfield Scott Hancock was able to roll up the Brigade’s flank and kill, wound or capture most of the men in the brigade.

     The 27th took part in over 70 battles, engagements and skirmishes, fighting in every major campaign fought by the Army of Northern Virginia. Their notoriety was earned at a high price, however. The strength of the 27th at Appomattox was 22, with only Sgt. Allen Neel and 2nd Cpl. Harvey Neel from Company D. Both of these men enlisted in 1861 shortly after First Manassas. A member of Company D, Pvt. Mike Foster, had the distinction of being honored as the "bravest and most efficient soldier in the Stonewall Brig." by Robert E. Lee in 1863. When he was captured in 1865, Gen. J.B. Gordon offered 50 Federal prisoners in exchange for Foster.