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David Gregg entered West Point in 1851 where two upperclassmen would play a huge part in his later years. In the class immediately ahead of Gregg was James Ewell Brown Stuart of Virginia. This was the famous "JEB" Stuart who, as the leader of the Confederate Cavalry, would someday be recognized as one of the most daring and resourceful leaders of cavalry in all time.

Sheridan combined his showmanship with his military talents and would later become one of U.S. Grant's favorite generals. These were traits foreign to Grant's own disposition. Under Grant, Sheridan would lead the Federal Cavalry to a large part of winning the Civil War, and later would be the leader of all the military forces of the United States under President Grant. David Gregg had no dramatics in his system, and had no particular admiration for those who did have a sense of showmanship.

Colonel Robert E. Lee became the Commandant of West Point during Gregg's second year at the academy. When Gregg's class started at West Point there were 71 Cadets in the class. Four years later 34 Cadets graduated in his class. The discipline and instruction at West Point must have been of the best kind to produce young warriors. The traits which appeared in these young warriors were found to persist through their military careers.

At West Point, the slender, six foot-one inch Cadet Gregg gained the reputation of being one of the best horsemen in the Corps of Cadets. David Gregg passed through his years at West Point without difficulty. At Commencement of 1854, Cadet Gregg met Miss Ellen Frances Sheaff of Reading, PA. She was on a trip with her aunt, Mrs. J.Pringle Jones, nee Catharine Hiester, and they stopped to see the festivities. Miss Sheaff was the granddaughter of former PA Governor, Joseph Hiester. David Gregg was the grandson of Senator Andrew Gregg, who had served in the Governor's cabinet. The matchmakers were busy. In eight years, Miss Sheaff was the woman that David Gregg would marry in a wartime wedding in Philadelphia.

In June 1855, David Gregg graduated from the military academy. He finished eighth in scholastic standing in his class, giving him some freedom of choice in selecting his place in the service. He chose the cavalry, and was assigned to Company C, Second Dragoons, in the Regular Army. He received a furlough which covered the summer months and then reported to Jefferson Barracks, Missouri. After serving as a drill instructor at Jefferson Barracks, he carried dispatches to New York. In Nov. 1855, he set out for Fort Union, New Mexico, arriving there in Feb. 1856. He was assigned to the command of Company H, First Dragoons, an experienced cavalry unit.

On May 16, 1858, Lt. David Gregg and his party of 160 men and officers found themselves surrounded by 1000 Indian warriors. It was his first major battle as a cavalry officer. After three days of severe fighting, including a fighting retreat, the unit had lost 2 officers and 5 enlisted men dead, 13 wounded and 3 missing. Lt. Gregg was in charge of the rear unit during the "fighting retreat" which saved the unit from almost certain massacre. It was the first of several battles for Lt. Gregg with the Indians.

On March 2, 1861, Lt. Gregg was promoted to First Lieutenant of the First Dragoons and ordered to return to Fort Tejon, California. Army officers on the west coast kept up with the events from Washington. Lt. Gregg supported James Buchanan, a Pennsylvania Democrat, and his platform of compromise. When Fort Sumter was attacked on April 12, 1861, dispatches went to all officers of the United States Army calling them to duty in the east. The officers suddenly faced a choice, lead Federal troops in putting down the rebellion, or resign their commissions. Lt. Gregg came east by the Panama route, giving up his stateroom to Captain and Mrs. Winfield Scott Hancock starting a life long friendship. Lt. Dorsey Pender also returned east, joined the Confederate Army and became the commander of the fomous "Light Division" of Confederate infantry before being mortally wounded at Gettysburg on July 2, 1863. The next day, July 3, 1863, David Gregg would meet JEB Stuart in a cavalry battle on the East Cavalry Field at Gettysburg.

Lt. Gregg arrived in Washington and found that he had been promoted to the rank of Captain and was assigned to the Third U.S. Cavalry. After a few months he was transferred to the Sixth Cavalry, an organization recruited in Pennsylvania, Ohio and New York in response to President Lincoln's proclamation of May 3, 1861. On October 12, 1861, Captain Gregg was stricken with a severe case of typhoid fever and was taken to a hospital on 'I' street in Washington. While he was there the building caught fire and he might have perished, an alert trooper in the same section saved him from the flames. In December 1861 he became engaged to Ellen Scheaff. He rejoined his regiment on Jan. 24, 1862 and then accepted the position of Colonel of the Eighth Pennsylvania Cavalry, a new regiment that included many Philadelphia area volunteers. He trained his men at Camp Leslie, VA, and proved to have a through understanding of handling cavalry troops. He adopted a method of weeding out the incompetent officers of the unit. It was a time of great stress and pressure, for the early battles of the war had disproved the theroy of the war ending quickly.

The Eighth Pennsylvania Cavalry took part in McClellan's Peninsular campaign, particularly in the Seven Day's Battle. During that fighting Col. Gregg's unit served as a screen that stood between the forces in gray and the retreating blue infantry. Col. Gregg showed steadiness under fire and led his troopers effectively. For the cavalry units which battled piecemeal with the infantry, it was particularly discouraging. After the war, Gen. Gregg spoke of "Cavalry misuse, which resulted mainly from lack of proper corps organization. Too often regiments would be attached to Corps and broken up to serve brigade headquarters instead of conserving its strength, it was wasted on useless details." For many months Col. Gregg mentioned how the Confederate Cavalry conducted the things that cavalry was suppose to do; raids on communications, capturing or destroying material or supplies, quick-hitting attacks in the opponents rear. He was determined to do something about it if he were ever given the authority to do so, use cavalry as cavalry and not as mounted headquarters escorts.

When Gen. McClellan war replaced by Gen. Burnside, a reorganization of the Army took place. Gen. Burnside attempted to reach Richmond by attacking Fredericksburg. At Fredericksburg the cavalry was held in reserve behind the attacking infanttry. Gen. George D. Bayard, who was the former Colonel of the 1st Pennsylvania Cavalry Regiment and was now in charge of the Brigade, was killed by an exploding artillery shell. Col. David Gregg was immediately appointed the Brigade Commanding Officer. Soon after the Battle of Fredericksburg, David M. Gregg was promoted to the rank of Brigadier General. Gen. Burnside was replaced and Gen. Hooker was the new commander of the Army of the Potomac. The Cavalry was combined into the Cavalry Corps under Gen. George Stoneman. Brig.Gen. Gregg was placed in charge of the Third Cavalry Regiment; Brig. Gen. Pleasonton was named the CO of the First Division; Brig. Gen. Averell was the CO of the Second Division; and Brig. Gen. John Buford was CO of the Reserve Brigade. It was the time for the Federal cavalrymen to take heart, they were to operate as an independent unit of the Army of the Potomac.

When Gen. Hooker began his attack on Gen. Lee's Army of Northern Virginia, he sent Gen. Stoneman on a raid around Lee's flank towards Richmond. Stoneman's Raid covered nine days and came within 18 miles of Richmond, causing much destruction in the rear of the Confederate Army. The object was to draw the Confederate Cavalry away from the Chancellorsville area, however Gen. JEB Stuart had the bulk of his force remain near the Fredericksburg - Chancellorsville area and proved to be a powerful weapon for Gen. Lee to inform him of the Army of the Potomac's movements. Gen. Gregg's Third Division was part of Stoneman's Raid. Shortly after the Federal defeat at the Battle of Chancellorsville, Gen. Hooker and Gen. Stoneman were replaced. Gen. Pleasanton took over as Commander of the Cavalry Corps and later Gen. Meade would take over the Army of the Potomac.

One of Gen. Pleasanton's early decisions was to attack the Confederate Cavalry Corps and seek information on Gen. Lee's troop movements. On June 9 the Federal Cavalry First Division and the Cavalry Brigade crossed the Rappahannock River at Beverly Ford under command of Gen. John Buford and headed for Brandy Station. While Buford attacked, Gen. Gregg led the Second & Third Divisions across Kelly's Ford and were to attack the flank and rear of the Confederates engaged with Buford.
Gen. Gregg's objective was to take Fleetwood Hill, where the Confederate Cavalry had their headquarters. The First New Jersey Regiment led the charge and held the Heights for a time but could not keep it. The fighting involved charge and counter- charge, and fierce hand to hand combat. When more Confederate cavalry arrived, Gen. Gregg and Gen. Buford withdrew to the north bank of the river. Information was received by Gen. Gregg to indicate the movement of the Confederate Infantry to the North, "the intended invasion of Maryland and Pennsylvania was discovered through Confederate dispatches captured" at Brandy Station. Confederate casualties were listed as 523 while the Union troops had 936, of which Gen. Gregg's Third Division had 376. From that time on, the Federal cavalry were to be rated as "worthy antagonists" by their opponents.On June 11, the Federal Cavalry was reorganized. The First Division was commanded by Gen. Buford and the Second Division was commanded by Gen. Gregg.

By June 15, Confederate Gen. Ewell had moved through the Shenandoah Valley and was in Pennsylvania heading northeast for Harrisburg. The Brandy Station battle delayed Gen. Stuart and Gen. Longstreet for six days. The Army of the Potomac turned northward and moved north, west of the Blue Ridge Mountains.

On June 17, Gregg's division met the Confederate Cavalry at Aldie with both sides taking severe losses.

On June 18, Gregg's division met the Confederates at Middleburg. Many of the First Rhode Island troopers were captured by Chambliss' brigade.

On June 19, Gregg's division met the Confederate troopers at Middleburg with Gen. Gregg's cousin, Col. J. Irvin Gregg leading the attack with his brigade.

On June 21, the Federal cavalry attacked again at Upperville. Gregg's troopers,w ith infantry support, were able to push the Confederates back to Ashby's Gap. These battles helped to keep the Army of the Potomac moving north toward Washington and into Maryland.

On June 27 the Union Cavalry crossed the Potomac River. On June 28, Gen. Meade replaced Gen. Hooker. Gen. Kilpatrick was appointed commander of the Third Cavalry Division, which was mainly composed of Michigan troopers. Two new Brigadier Generals were appointed in the Third Division, Gen. Elon Farnsworth and Gen. George A. Custer.

On June 30, the new Third Cavalry Division troopers met Gen. Stuart's Cavalry at Hanover, PA. The Confederates withdrew and headed to York to meet Gen. Early. With the way to Gettysburg blocked by Union cavalrymen, Gen. Stuart headed northwest to Carlisle, where on July 1 he attacked and burned the Cavalry Barracks. He arrived in Gettysburg late on July 2nd, missing the battle for the first two days.

Gen. Gregg's troopers took part in the cavalry battles on the East Cavalry fields of Gettysburg

On June 11, the Federal Cavalry was reorganized. The First Division was commanded by Gen. Buford and the Second Division was commanded by Gen. Gregg.

On June 17, Gregg's division met the Confederate Cavalry at Aldie with both sides taking severe losses.

On June 18, Gregg's division met the Confederates at Middleburg. Many of the First Rhode Island troopers were captured by Chambliss' brigade.

On June 19, Gregg's division met the Confederate troopers at Middleburg with Gen. Gregg's cousin, Col. J. Irvin Gregg leading the attack with his brigade.

Gen. Gregg's troopers arrived at the intresection of Low Dutch Road & Hanover Road shortly after noon on July 2. Gregg's troopers were assigned to protect the right flank and rear of the Union Army.

David Gregg resigned his commission in the army in a letter to the Adjutant General of the United States, dated Jan. 25, 1865. The letter stated: "Having for more than three years been on uninterrupted service in the field, commanding cavalry in the Army of the Potomac, I at this time find such an imperative demand for my continued presence at home that my personal attention may be given to pressing private duties and business, that I can no longer defer action to secure my discharge from the service."

He was too proud to explain, but whatever may have been the real cause, it is only fair to add that it cost the army in its closing campaign the services of a most gallant and useful officer.

By leaving the army when he did, David Gregg missed the spring campaign that ended with the surrender of Lee's army at Appomattox Court House, April 9, 1865. Sheridan's cavalry, including Gregg's old division, played a big part in moving by the left flank and thus forcing Lee to abandon the forts at Petersburg. These movements followed the pattern set by Gregg himself, under Gen. Grant's authority. His men remembered him as an officer always to be found at the point of greatest danger, one who could not only lead them into battle, but also bring them safely out.

The Civil War in the Shenandoah Valley