Gaylord received the Congressional Medal of Honor, the highest award for bravery and heroism during combat, for his actions during the Civil War at the Battle of Fort Stedman in Petersburg, Virginia, on March 25, 1865. The opening line of every Medal of Honor citation tells the story: "For conspicuous gallantry and intrepidity at the risk of life above and beyond the call of duty." Note the gold leaf on the crest of Gaylord's military monument.
As the story goes, Sergeant Gaylord was with Company A, 29th Massachusetts Infantry, during the Petersburg Campaign and in the final days of the Civil War. The Confederate Army and General Robert E. Lee were in Richmond, Virginia surrounded by the Union Army. Both armies aimed to take Petersburg, a rail hub outside of Richmond that controlled the lines of communication and supply routes into the Confederate Capital. In short, if you owned Petersburg, you owned Richmond. The Confederate Army decided to make one last attempt to break the Union lines around Richmond and Petersburg. However, the Confederate Army did not have the men or material to match the Union Army and without one dramatic, sweeping victory, the war would be lost. It was against this backdrop that Gaylord was called into action.
In a pre-dawn assault on March 25, 1865, Confederate forces overwhelmed the defenses at Fort Stedman and created a massive gap in the Union line. They attacked until they reached Fort Haskell, where the retreating Union forces tried to re-organize with some elements from the 29th Massachusetts Infantry. With little time, Captain John Deane, Commander of the 29th Massachusetts, spotted an abandoned artillery piece on the left flank of the advancing Confederates. He moved Sergeant Gaylord and another soldier into position. Together, they operated the artillery piece while openly exposed to enemy fire. They delivered devastating volleys into the Confederate ranks, pushing them back beyond the original limits in front of Fort Stedman.
Within two months of the Battle of Fort Stedman and Gaylord's heroism, Robert E. Lee signed the Confederate surrender at Appomattox Court House, and the Civil War was over. The victory at Fort Stedman was a critical point in finishing the war.
Levi Gaylord received the Congressional Medal of Honor on June 22, 1896.
