Harry Ward Gilmor was born into a life of luxury and affluence on January 24, 1838. He was one of eleven children. Harry and his family lived at “Glen Ellen Castle” in Towson, Maryland. His home was a three-story early Gothic Revival mansion, with towers on three corners, meant to resemble Abbotsford, a Scottish castle owned by Sir Walter Scott. It sported a guest house constructed in the likeness of a Greek temple and a gatehouse that was designed to look like a Gothic ruin.
In harmony with his upbringing, Harry spent his childhood dreaming of knights, noblemen, chivalry, and glory in battle. Much of his early adulthood, however, was spent homesteading in Wisconsin and Nebraska. Still, when the threat of civil war loomed in early 1861, Harry returned to Baltimore to do his duty.
Upon his return, Gilmor joined the newly formed Baltimore County Horse Guards as a corporal. In consequence to the efforts of the residents of Baltimore to prevent the passage of Federal troops through the city, the Horse Guards were given orders to burn several bridges north of the municipality to prevent Northern troop movements through Baltimore.
Harry Gilmor’s activities did not endear him to the Federal occupation troops in Baltimore commanded by Brigadier General Benjamin Butler. Gilmor was one of several individuals arrested and imprisoned in the “Baltimore Bastille,” commonly known as Fort McHenry. Marylanders, suspected of being Confederate sympathizers, were imprisoned there. Most were never charged with a crime and many were never brought to trial. Others were released after pledging not to “render any aid or comfort to the enemies of the Union,” or by taking an oath of allegiance.
Following Gilmor’s release in August 1861, he journeyed south and joined the command of Colonel Turner Ashby. Harry would serve with Ashby in the 7th Virginia Cavalry throughout Jackson’s 1862 Valley Campaign. On several occasions he was even placed on special assignment to General Stonewall Jackson.
General Jackson had always dubbed Turner Ashby’s cavalry command “a mob.” Whereas most cavalry regiments had ten companies, Ashby’s 7th Virginia regiment had twenty-five. On April 24, 1862, General Jackson attempted to divide Ashby’s oversized command into more manageable pieces. Jackson assigned thirteen companies to Brigadier General Charles Winder’s Brigade. Companies A through K were placed under the direction of Brigadier General William Taliaferro. Ashby was to retain command of only a small fragment of his original regiment, and this was only to act in the role of both advance and rear guards.
Colonel Ashby was so outraged by the incident he submitted his resignation. Ashby even considered challenging Stonewall Jackson to a duel. Fortunately, calmer minds prevailed, and Colonel Ashby was allowed to retain his command. Jackson would write to General Robert E. Lee on the subject stating: “Such was Ashby’s influence over his command that I became well satisfied my attempt to increase the efficiency of the cavalry would produce the contrary effect.”
On June 16, 1862, ten days after Turner Ashby’s death, “the long awaited” reorganization of Turner Ashby’s cavalry command took place at Conrad’s Store. Ten companies were retained to constitute the 7th Virginia Cavalry; also known as the 1st Regiment of Ashby’s Cavalry. Ten more companies were designated as the Twelfth Virginia Cavalry, or the 2nd Regiment of Ashby’s Cavalry. Harry Gilmor would be commissioned Captain in Company F of this unit. The remaining five companies would be designated as the 17th Battalion of Virginia Cavalry.
On May 27, 1863, Harry Gilmor was promoted to the rank of Major and asked to raise an independent battalion of cavalry. Before he could complete this assignment, though, the Gettysburg campaign interceded. During the battle, Major Gilmor was assigned command of the First and Second Maryland Cavalry, in General George Steuart’s Brigade. Major Gilmor was delegated the job of Provost Marshal for the town of Gettysburg during its brief occupation.
By the Spring of 1864, Harry Gilmor was assigned to independent command in the Shenandoah Valley. Gilmor recognized that in order for his 2nd Maryland Cavalry to survive in occupied territory he needed the support of local citizens. Without safe hiding places, and other means of support, Gilmor’s effectiveness would be severely weakened. It was during the month of May that Harry found himself operating behind enemy lines in the region outside of Winchester near Newtown, or what is now Stephens City, Virginia. It is the second oldest town in the Shenandoah Valley, trailing only behind Winchester.
In his memoir, written forty-one years after the war, John M. Steel characterized the wartime situation of the town as being “between the lines. Newtown became a no-mans-land for much of the war. It was close enough to suffer the effects and disruptions to daily life that came with the Federal troops’ occupation of Winchester and the surrounding region, but distant enough to return to limited Confederate control after nightfall.”
An incident that had occurred in Newtown on May 30, 1864, threatened the continued existence of the town. Major Gilmor had received a report on the 29th that Lieutenant Colonel Augustus Root of the 15th New York had left Martinsburg, West Virginia, southbound, as part of an escort detail for sixteen Union supply wagons. Noted Winchester diarist Mary Greenhow Lee had observed the passage of these wagons through town on the afternoon of May 30. Someone passed this information on to Gilmor, who decided an attack on the wagon train was essential. Newtown, with its narrow main street, was the perfect place for an ambush.
Gilmor and his men concealed themselves in the woods near Bartonsville, just north of Newtown. As the train of wagons passed, Gilmor and a detachment of his 2nd Maryland Cavalry Battalion pounced on the rear of the formation, and charged south along Main Street. Gilmor hoped the unexpected attack would cause the wagons to stampede and neutralize any soldiers that might have been concealed in the wagons.
Surprised, Root’s men retreated south through town and setup a defensive position behind the house belonging to Dr. McLeod. In the process two of the wagons upset and blocked the bridge across Steven’s Run along the Valley Pike. Several of the wagons, however, were still able to race on toward Middletown.
Region of the Shenandoah Valley in which Gilmor Operated.
In the assault, Gilmor’s horse bolted in the excitement and carried him down the pike in the direction of the lead wagon. As he passed through the wagon train in his mad dash, several members of the 15th New York Cavalry took the opportunity to swing their sabers in his direction. Though Gilmor received several saber cuts he was not seriously wounded. Fortunately, all of the pistol shots directed at him missed as well.
When Gilmor reached the lead wagon he swung his sword at the lead horse and was able to disable it, causing the wagon to bound off the pike. All of the wagons following it were forced to abort their dash toward safety. Having stopped the train and having regained control of his horse he jumped the stone wall that paralleled the Valley Pike and headed back into town.
Gilmor’s men had fared very well. They had skirmished with members of the 15th New York and routed them. The defenders, having gathered near Dr. McLeod’s home, had been defeated as well and many men in blue had been captured. The Confederates pilfered everything of value from the wagons and then proceeded to set them on fire. After tending to the dead and wounded, Gilmor retreated with four wagons, forty prisoners, and seventy horses.
As Gilmor rode out of town with his bounty, a train of sixty wagons escorted by six hundred infantry rolled in. Mary Greenhow Lee apparently entered town on the heels of this second wagon train. She was passing through the community in order to attend a funeral at the Barton’s home at Vaucluse. She noted: “Four miles from town there was a cry of Yankees ahead. As we approached, we found it the advance guard of a double wagon train – about 200 wagons & an escort of 500 men. We passed the houses Hunter had burned last week, & then saw some horsemen ahead of us; I saw at a glance they were Confederate & we stopped to talk to them. Told us Gilmor had captured the whole wagon train that had passed through yesterday evening.”
As the group continued through town one of the Confederate soldiers stopped them and informed them they had captured a Union soldier in the act of burning a local house. He was caught “firing a house … in retribution for Mosby’s shooting at the wagons.” The ladies, not wishing to witness the act, scooted through town and on toward their destination..
Mrs. Lee noted as they “passed out of Newtown, we drove by 16 wagons burning on the road; several dead horses &, to my infinite horror the bodies of two dead Yankees who had been shot this morning; involuntarily I covered my eyes that the sight might be excluded.”
Major General David Hunter, commanding Union forces in the area, had previously ordered three houses burnt in Newtown in retaliation for the attacks that had taken place earlier in the week. Hunter was informed of the second attack in Newtown that same evening. General Hunter, tired of the repeated assaults on his supply trains in the area, determined something had to be done right away.
Sign Noting the Orders to Burn Newtown, now Stephens City. Major Stearns Last Name is Misspelled on the Sign.
On the 30th General Hunter dispatched Major Joseph Stearns and a detachment of 200 men from the 1st New York Cavalry Regiment from his army at New Market. Their orders were to “proceed to Newtown tomorrow morning at 3 o’clock, for the purpose of burning every house, store and out-building in that place.” He was only to spare “churches, and the dwelling of Doctor Owens, who had been kind to the Federals.”
As the cavalrymen trotted north along the Valley Pike, they could not help but notice the exposed graves of the Union dead on the New Market Battlefield; a contest that had taken place just two weeks before. It was evident many of the “confederate burial details were tired, and the ground was muddy from all the rain. Some of the dead had only been covered with a few inches of dirt. The rains had washed what little soil had been scuffed over them. The smell of decaying bodies was overwhelming.”
As the New Yorker’s neared Newtown, Major Stearns revealed their mission to his troopers. “The men became sullen and talked of refusing to obey the order. The children and elderly of the town, aware of Hunter’s threat, helplessly stood in their doorways. Major Stearns met with the elders of the town, who protested that they had no control over the Confederate raiders and that they had cared for Federal wounded from the attack.”
In addition, Major Stearns spotted a note which had been posted as a warning to General Hunter. The note advised him not to burn the town. Gilmor promised to retaliate by hanging “thirty-five men and six officers and send their bodies to him in the valley.”
Stearns consulted with his troopers and it was decided they would spare the town. Stearns determined he would risk Hunter’s wrath and his own military career rather than burn the homes of civilians. He spared the town on the provision the local citizens would take the Oath of Allegiance. This they did.
Major Stearns returned to face a searing reprimand from General Hunter. It was General Hunter’s Chief of Staff, David Strother, however, who saved Stearns from dismissal for disobeying orders. Hunter let his actions stand and allowed him to retain his command. The historic buildings, which can still be seen in Stephens City today, are a testimony to a different kind of Civil War heroism; the gallant act of compassion.
Harry would go on to distinguish himself with several significant cavalry excursions. His most famous raid, known as the Magnolia Train Raid, occurred later in July 1864, during General Jubal Early’s assault on Washington D.C. During his raid on Baltimore, Gilmor and 135 troopers disrupted telegraph communications, destroyed railroad tracks and trestles, and captured two trains. One of the train passengers, and subsequent detainees, was Major General William B. Franklin. The raid was extremely successful, and Gilmor always claimed he could have captured Baltimore itself if he had desired.
Following the war Harry would return to Baltimore. He would serve as police commissioner for five years and later as the city’s mayor. He died in March of 1883, a war hero, from complications caused by a wartime injury to his jaw. “Gilmor’s funeral was a large local ceremonial event with many dignitaries present to honor this war hero.” Prior to his passing, he wrote and published a war memoir entitled Four Years in the Saddle. It is well worth read.
Armstrong, Richard L. 7th Virginia Cavalry. H. E. Howard. Inc. Lynchburg, Va. 1992.
Bonnell Jr., John C. Sabres in the Shenandoah: The 21st New York Cavalry, 1863-1866. Burd Street Press. Shippensburg, Pa. 1996.
Brown, Peter A. Mosby’s Fighting Parson: The Life and Times of Sam Chapman. Willow Bend Books. Westminster, Md. 2001.
Mahon, Michael. Winchester Divided. The Civil War Diaries of Julia Chase and Laura Lee. Stackpole Books. Mechanicsburg, Va. 2002.
Straader, Eloise C. The Civil War Journal of Mary Greenhow Lee. Winchester County Historical Society. Winchester, Va. 2011.
Walker, Gary C. Hunter’s Fiery Raid through Virginia Valleys. Second Edition. A & W Enterprise. Roanoke, Va. 2004.