During the winter of 1863-1864, a plan was thought of by Confederate General Robert E. Lee to send a force to Point Lookout, Maryland to free the thousands of Confederate prisoners being held there. However, by late February, Lee’s plan was interrupted by the Dahlgren and Kilpatrick Raid on Richmond. As June 1864 began, General Lee sent out Lieutenant General Jubal Early to strike upon the Shenandoah Valley, to relieve pressure from his entrenched lines near Petersburg, Virginia, There Lt. Gen. Early secured Lynchburg, and began marching north to Maryland. As Lt. Gen. Early made his way to Staunton, Virginia, General Lee began evaluating his Point Lookout plan. Lt. Gen. Early was fully aware and in communication with General Lee about this daring raid.
The raid itself called for a force that would travel upon land, while another force sailed by sea into the Chesapeake Bay. The two forces would have to be precise in their arrivals to Point Lookout. General Lee wanted this force to be led by Marylanders. Bradley Johnson and his cavalry brigade were picked by General Lee. Brigadier General Bradley’s cavalry brigade contained two Maryland consolidated cavalry units, commanded by Major Harry Gilmor.
As Lt. Gen. Early neared the Potomac River on July 2, near Petersburg, Virginia, General Lee summoned Confederate States Naval Commander John Tyler Wood to his headquarters. Commander Wood was also a Marylander, and he was selected by General Lee to lead the naval expedition to Point Lookout. Commander Wood was to gather supplies and guns, as well as lead his force on the beach, and upon landing he and Brig. Gen. Johnson would attack the prison at Point Lookout. Up until this point only Lt. Gen. Early and Commander Wood knew of the raid.
As Brig. Gen. Johnson’s cavalry led the way for Lt. Gen. Early’s army in Maryland on July 7, he fought along the way from Middletown to just west of Frederick. The next evening, he was ordered to Lt. Gen. Early’s headquarters, where the plan was laid out before him. Brigadier General Johnson was to first make his way toward Baltimore, cutting all communications and railroad lines from the city to the north and move due south toward Washington, and from there, move directly to Point Lookout to help free the Confederate prisoners. A total of about two hundred and fifty to three hundred miles had to be traveled, and this had to be accomplished in three days, by the evening of July 12. Brigadier General Johnson was stunned at the idea.
During the night, Johnson’s cavalry made their way to Worman’s Mill on the Liberty Road, and bivouacked there for the night. As morning came on July 9, the sounds of battle were heard as the main body of the Confederate army began to attack the Union forces at Monocacy Junction. This was the signal that Brig. Gen. Johnson was waiting for, and he began moving along the Libertytown Road. The Confederate cavalry made their way through Libertytown and Uniontown before halting just within sight of New Windsor, when at dusk they would enter the town. Major Gilmor’s cavalry was ordered to screen ahead to Westminster.
As the Confederates neared their first targets, railroad bridges were destroyed, and telegraph wires were cut. While Major Gilmor was in Westminster, Brig. Gen. Johnson sent a dispatch ordering him to obtain 1,500 sets of clothing. Brigadier General Johnson moved into Westminster, where Major Gilmor personally asked him to spare the town from the torch. During the night, Brig. Gen. Johnson began initiating the second phase of the raid. They would begin moving toward Baltimore.
During the early morning hours of July 10, Major Gilmor was ordered to take his command and proceed to Cockeysville, where he was ordered to tear up railroad tracks, destroy two bridges along the Northern Central Railroad, and the turnpike bridge. Major Gilmor also placed pickets on the road leading toward Baltimore. Brigadier General Johnson reached Cockeysville during the mid-morning and linked up with Major Gilmor. There, Brig. Gen. Johnson ordered Major Gilmor to take one hundred and thirty-five of his Maryland command to destroy the Gunpowder River Bridge. Major Gilmor was upset that he could not take his full five hundred Marylanders with him since he heard that the bridge was heavily guarded.
Major Gilmor left Cockeysville at noon, and by evening had rode through Timonium, cutting telegraph lines along the way. Near Kingsville, a local farmer named Ishmael Day, shot one of Major Gilmor’s men as he took the Union flag down from his property. After he shot the soldier, farmer Day fled into the woods escaping Gilmor’s men. In retaliation, farmer Day’s house and barn were burned. While Major Gilmor was riding off, Brig. Gen. Johnson’s brigade eventually moved through Green Spring Valley, encamping at sunset, twelve miles northwest of Baltimore.
At 4:30 a.m. on July 11, Major Gilmor struck Magnolia Junction, one mile northeast of Gunpowder Bridge. Telegraph wires were quickly cut. By 9:30 a.m., an inbound train came rolling in, and stopped by Gilmor’s men. They learned that Union Major General William Franklin was on board, and he was quickly taken prisoner. Other Union troops were captured and quickly paroled.
While waiting for another train to roll in, the men disabled the first train. Soon another train rolled in and it was captured, set on fire, and moved on top of the Gunpowder Railroad Bridge. As the train itself, burned, the bridge quickly began to ignite, soon becoming engulfed in flames. By 4:00 p.m., Major Gilmor left and moved along the York Road. He thought about entering into Baltimore, but moved westward instead to Towsontown, arriving there late in the evening. Major Gilmor continued to Owings Mills and Randallstown. During the night, Maj. Gen. Franklin escaped from custody.
During the same morning, Brig. Gen. Johnson had ordered a detachment of the 1st Maryland Cavalry to burn Maryland Governor Augustus Bradford’s home. The Marylander’s arrived at 9:00 a.m. and fired the house. Brigadier General Johnson continued to move through Owings Mills, Woodstock, Ellicott’s Mills, and encamped at Triadelphia, twenty miles southwest of Baltimore. Near Owings Mill, at Painter’s Mill, the Confederate horsemen noticed the frozen treat of ice cream being loaded into freezers on a wagon headed to Baltimore. The Confederates quickly took the frozen treat and issued it for breakfast. During that hot morning, the men ate the frosty treat, or tried to place it in their canteens so that it would melt and they could drink it later.
At Baltimore, the Union army, under the command of Major General Lew Wallace was given a new commander, Major General E. O. C. Ord. Soon, the Union commander took his newly acquired command and began garrisoning several of the forts. During the day, Brigadier General Johnson had sent a courier to gather information on the layout of the city. The courier reported back by midnight with information that the remainder of the Union XI and XIX corps were moving toward Washington to reinforce the ring of forts. This information was quickly sent to Lt. Gen. Early who was already at Fort Stevens.
All the Confederate activity did not go unnoticed by the War Department. They had received word about a Confederate raid to free the prisoners held at Point Lookout. The garrison was notified, and the U.S. Navy stepped up patrols in the Chesapeake Bay and along the Atlantic Ocean. Upon learning this, Lt. Gen. Early sent a dispatch to Brig. Gen. Johnson notifying him that the raid was off, and he was to move at once toward the main body of the Confederate army. Commander Wood was also notified to call off his part of the Naval expedition.
On July 12, Major Gilmor operated around Pikesville. He sent a small detachment of men to operate near the Baltimore city line, cutting telegraph lines and disrupting communications. After accomplishing his goals, Major Gilmor began moving westward to unite with Lt. Gen. Early’s army at Poolesville, where he arrived on July 13.
At 2:00 a.m., Brigadier General Johnson continued to move toward Beltsville, arriving there at 9:00 a.m. After doing some major damage there, Brig. Gen. Johnson moved to Upper Marlboro. Along the way at Bladensburg, Brig. Gen. Johnson attacked about five hundred Union cavalry. During the afternoon, a courier from Lt. Gen. Early informed Brig. Gen. Johnson that the raid on Point Lookout was called off, and he was to report back to the main body of the Confederate army.
After following the line of defenses around Washington, the advance units of Johnson’s brigade reached the Confederate headquarters at Silver Springs. Brigadier General Johnson arrived just after midnight, in time to form the rearguard of Lt. Gen. Early’s army as he moved away from the defenses of Washington.
The Johnson and Gilmor Raid had accomplished destroying vital communication lines, and the destruction of bridges, it was, by far, a huge success. Although, Johnson fell behind by one day, he was in striking distance of Point Lookout. Johnson and Gilmor were both criticized for taking time to visit family or friends during the raid, which is where several hours were lost. Also, the destruction of vital military targets consumed a lot of their time.
Although he was the hero of Monocacy, Union Maj. Gen. Wallace, was criticized for his lack of pursuance while the Confederate army was in Maryland marching upon the National capital, Baltimore, and the surrounding suburbs.