Harry Gilmor was born January 24, 1838 at "Glen Ellen", the family estate in Baltimore County, Maryland. He was educated under a private tutor, and engaged in business in Baltimore and in the West. After homesteading in Wisconsin and Nebraska, he returned to Maryland in time to join the newly formed Baltimore County Horse Guards as a corporal.
He was tall, handsome, a polite gentleman, a member of Maryland's high society, and as
personally brave as "William Wallace" of Scottish lore. He was also extremely conceited and full of self assurance. These ingredients made him one of the most dashing cavalier horsemen of the war. After the efforts of the citizens of Baltimore to prevent the movement of Federal troops through the city, the Horse Guards received orders to burn several bridges north of the city to prevent further troop movements toward Washington City. Following the occupation of Baltimore by Federal troops under Brigadier General Benjamin "Beast" Butler, Gilmor was one of many to be arrested and imprisoned in Fort McHenry. After his release he made his way to the Shenandoah, where he served as a scout for Colonel
Turner Ashby. Private Gilmor was soon promoted to Sergeant Major for gallantry after the action at Harper's Ferry in December, 1861. In February, 1862, he was severely wounded. By March of 1862 he had raised his own
company, which was attached to the 12th Virginia Cavalry. Gilmor was with Stonewall Jackson at
McDowell in May of 1862. After the battle he was directed to follow
Milroy and round up stragglers. Afterwards he was directed to find and watch General
Fremont. When Fremont began his movement to come in behind Jackson while Jackson was busy dealing
with Shields at the northern end of the Valley, Gilmor alerted Jackson. This information allowed Jackson to change his plans, move to the east fork of the
Shenandoah, where he defeated Shields at Cross Keys on June 8th, and Fremont at Port Republic on June
Gilmor's Company spent the next three months scouting, serving as couriers and
harassing enemy camps and trains. True to form, when Jackson's column crossed the Potomac into Maryland in September of 1862, Gilmor, expecting the Federal army to be slow to react to Lee's invasion, took "French Leave," to see his family in Towson, Maryland, just north of Baltimore. He and a companion managed to ride to within seven miles of Glen Ellen, Gilmor's family home. It was late, so the two riders decided to spend the night at a friend's home. Unknown to them, a Federal patrol was on it's way to the friend's home to look for contraband and supplies moving South. As a consequence, Gilmor found himself once again a guest of the Federal government. He spent five months in prison. Exchanged in February, 1863, Gilmor aligned himself with JEB Stuart, and was at his side during the Battle of Kelly's Ford in March of 1863. But it wasn't long before he petitioned to raise his own regiment of cavalry. In April of 1862 the Confederate Congress had passed an act authorizing the creation of partisan groups to operate independently of established military field commands. This type of operation fit Gilmor's character perfectly. He began to organize several companies consisting mostly of Marylanders. "The Band," as they commonly called themselves, were a rough and ready lot of freebooters who often operated behind enemy lines. On May 27, 1863, Gilmor was promoted to the rank of Major.
He participated in the Battle of Brandy Station and was sighted in the after action reports of General Fitzhugh Lee and General J.E.B. Stuart for his conduct in this engagement. From time to time Gilmor's Battalion became aligned with other groups, most commonly McNeill's Rangers, and the 1st Maryland Cavalry. During the Confederate move down the Valley into Maryland in June of 1863, Gilmor found himself in temporary command of the 1st Maryland Cavalry, it's commander having been wounded. He was involved in action around Winchester, and was directed to lead part of his command toward Harper's Ferry to capture General Milroy, but came up empty handed. Gilmor's men were involved in the
operation to collect food stuffs and horses for the Army of Northern Virginia in Pennsylvania during Lee's move north. The cavalry was
assigned various provost duties, courier duties and provided support for artillery, but saw no direct action at Gettysburg. During the battle, Major Gilmor was assigned command of the First and Second Maryland Cavalry, under General
George Steuart's infantry brigade. He captured and held for a few
days Frederick, Maryland, and the towns of Chambersburg, Carlisle, and Gettysburg, and was appointed provost-marshal of the last-named place. When the Confederate army returned to Virginia Gilmor returned to the Shenandoah. By September he had six full companies of partisan rangers engaged in hit and run attacks on Federal wagon trains, railroads, telegraph lines, depots, bridges and encampments. His command's area of operation was the Shenandoah Valley and parts of
West Virginia. In February, 1864, he raided on the Baltimore and Ohio railroad, and was court-martialed for destroying a train and permitting his command to rob the passengers; but he was honorably acquitted of this charge and restored to his command
In May of 1864 the Confederate Army made it's final attempt to establish a "Maryland Line." Gilmor was ordered to deliver his command to General
Arnold Elzey in Staunton. In typical Gilmor fashion, he failed to report. He remained an independent command,
harassing Federal activity. During this period he often aligned himself with Generals
Imboden and McCausland, and as a result was with them as they defended the Valley against
Sigel. The 2nd Maryland was at New Market but not heavily engaged, their primary mission being
After the defeat of Union Major General Lew Wallace at Monocacy on July 9, 1864, Gilmor's command acted as the spearhead for the raid around Baltimore in 1864 with General
Bradley T. Johnson's infantry command. Gilmor's dash on Baltimore was one of the most hazardous and impetuous adventures of the war. At one point he ensured the safe passage of his raiders by posing as a Federal scout trying to hunt them down! While assigned to scout duty under General Jubal Early, Colonel Gilmor single-handedly captured a company of Federal infantry. Gilmor and Holmes Conrad, a man under his command, later captured more than 50 troopers from the 1st New Jersey Cavalry.
Colonel Gilmor was ordered by General Early to take his command to Hardy County, West Virginia. He was to combine with other partisans in the area and attack the Baltimore & Ohio Railroad. Colonel Gilmor was finally captured while defending his guns in Hardy County, on February 4, 1865. He remained a prisoner at Fort Warren until July 24, 1865. During that time he compiled a series of historical sketches about his career which were later developed into "Four Years in the Saddle" (New York, 1866).
For several years after the war, Harry Gilmor lived in New Orleans, where he married Miss Mentoria Strong. Upon his return to Maryland, he was elected colonel of cavalry in the Maryland National Guard. He also served as Baltimore City Police Commissioner from 1874 to 1879. He was a member of the Society of the Army and Navy of the Confederate States in Maryland and it's Vice-President in 1882. Harry Gilmor died in Baltimore on March 4, 1883 at the age of forty-five.
He was interred on "Confederate Hill" in Loudon Park Cemetery.