Tuesday, March 15, 2016

How 20-year-old Connecticut Yankee saved army in Virginia

From Hartford, Conn., Charles Greenleaf served in the 5th New York Cavalry. He was
mortally wounded at Kearneysville Station, Va., on Aug. 25, 1864.
(Connecticut State Library)

Adapted from my latest book, Hidden History of Connecticut Union Soldiers. E-mail me here for information on how to purchase an autographed copy.

On May 23, 1862, Charles Greenleaf, a 20-year-old soldier from Hartford, accomplished what few Yankees could claim: He was credited with helping save a Union army. With a series of lightning strikes, Stonewall Jackson’s foot cavalry booted the Federals from the Shenandoah Valley in Virginia that spring, routing them at McDowell, Strasburg, Front Royal and Winchester, before chasing Nathaniel Banks’s army across the Potomac River and into Maryland.

It could have been worse.

With the outnumbered Yankees in imminent danger of being crushed near Front Royal, a Union colonel ordered Greenleaf, a sergeant in the 5th New York Cavalry, to take another soldier, grab two of the fastest horses in Company D and ride like hell to seek reinforcements from Banks at his headquarters in Strasburg. The direct route was blocked by Rebels, so Greenleaf  took another road, riding seventeen miles in fifty-five minutes.

General Nathaniel Banks
When an exhausted Greenleaf got to Banks’s headquarters, the general did not think the Union situation was perilous, so he only sent a regiment of infantry and two pieces of artillery to the colonel’s aid. “I asked General Banks for a fresh horse to rejoin my company,” Greenleaf wrote to his parents, “and he gave me the best horse that I ever rode.”

On his way back, apparently without his comrade, Greenleaf saw two men standing in the Front Royal Turnpike, about two miles from his destination, with their horses resting by a nearby fence. Believing they were Union pickets, Greenleaf asked the men who they were.

“We are part of Gen. Jackson’s staff,” they replied.

Thinking they were joking, Greenleaf laughed and asked the men where he could find the famous Stonewall Jackson. In advance, said the Rebels, who were unaware of Greenleaf’s allegiance and let him ride farther down the road. In amazing bit of bad/good fortune, the wayward Yankee soon encountered  another  Rebel, a soldier in the 8th Louisiana. Unaware that he was in the presence of a Union soldier, the Confederate was asked by Greenleaf  how many Rebels were nearby.

“20,000,” he replied.

“I turned back and drew my revolver,” Greenleaf wrote, “expecting either a desperate fight or a Southern jail. But the officers in the road didn’t stop me, and I was lucky enough not to meet any of their pickets. But if it was not a narrow escape, I don’t know what is.”

Greenleaf quickly rode back to Banks’ headquarters to inform the general about his surprising military intelligence. Fearing that Jackson would outflank his army, Banks soon had his soldiers on the move up the Valley Pike toward the supposed safety of his base in Winchester. “He said I saved the Union army,” Greenleaf wrote to his parents about the general, whose men were ordered to destroy thousands of dollars’ worth of valuable supplies in Strasburg to prevent them from getting into enemy hands.

In a letter home to his parents, cavalryman Charles Greenleaf drew this image of himself riding a horse.
(National Archives)
During his short military career, Greenleaf ventured all over the war zone in the East, from Harrisburg, Pennsylvania, in the north to war-torn towns throughout Virginia. As a private in the 1st Connecticut -- he was one of the first soldiers in the state to join the Union army -- he hugged the ground while he listened to artillery explosions and thud of shells strike near him during the First Battle of Bull Run on July 21, 1861.

Greenleaf survived the first major battle of the war, and when his three-month term of service in the 1st Connecticut elapsed, the youngest of four children of Mary Ann and William Greenleaf re-enlisted, joining the 5th New York Cavalry. “I cannot get anything to do at my business” and his father was sick, Greenleaf told an acquaintance, so the Union army was his best option.  Before the war, Charles was employed as a chaser at Rogers Silver Plate Co. in Hartford, while his father worked as a bookbinder.

In lively war-time letters to his parents, Greenleaf wrote of a brush with death when he fell from his wounded horse during a charge on a battery, the disappointment of not being promoted and his hope that his father would give one of his photos to another man to put in the Neptune Company firehouse, where he also had worked.

 And he told of the ugly realities of Civil War.

Connecticut Historical Society collection

“I have been in the service a year, but I never knew what war meant till to-day."

-- Charles Greenleaf on the aftermath of the Battle of Antietam (above)

“I have been in the service a year, but I never knew what war meant till to-day,” he wrote in a letter to his parents on September 20, 1862, about the aftermath of the Battle of Antietam. He recalled observing more than 100 amputated arms and legs heaped in a yard by a hospital and dead Rebels piled “like cord-wood” along both sides of a road for two miles. “They have lain there two days in the sun,” he wrote, “and are all bloated.”

Nearly three months later, while stationed near Manassas, Virginia, he saw similar gruesome sights at the old Bull Run battleground, where he had fought in the summer of 1861 and where the two armies clashed shortly before Antietam.  Union dead were still scattered about, their skulls and hands sticking up through the ground. In the high grass, he saw skeletons of some Yankees who hadn’t even been buried.

Less than two years later, Greenleaf would join them.

On August 25, 1864, at Kearneysville Station, Virginia, the 5th New York Cavalry was attacked by a Rebel force that outnumbered the Yankees 30-to-1, according to one of Greenleaf’s comrades from Hartford. “Our little battalion was under the sharpest fire we ever experienced,” recalled Lt. Henry Appleby, whose fellow cavalrymen temporarily held off the Rebels with their seven-shot Spencer carbines. Wounded in the left side during the skirmish, Greenleaf was carried off the field, placed in an ambulance and transported more than 15 miles to U.S. General Hospital in the hamlet of Sandy Hook, Maryland, along the Potomac River. A day later, he died there at about 5 p.m.

“Your loss is our country’s loss, too,” an 18th Connecticut chaplain wrote to Greenleaf’s parents on August 27, 1864. A letter from his mother, his commission as lieutenant and the rest of Charley’s effects, Rev. W.C. Walker noted, would be forwarded home.

After Greenleaf’s death, the Neptune Engine Co. 2 members passed six resolutions and submitted them to the local newspapers. The firehouse, one of the resolutions read, was to be draped in mourning for 30 days.


Lieutenant Henry Appleby of the 5th New York Cavalry wrote this letter to Greenleaf's father about  Charles' wound during a battle at Kearneysville Station, Va.:
Connecticut Historical Society collection
Near Boonsboro, Md.
Aug. 27th/64

Dear Sir:

It is my melancholy duty to inform you that Charles was severely wounded the day before yesterday in an engagement with the enemy between Shepherdstown & Charlestown, Va. His wound is in the left side. I saw him carried off the field and placed in an ambulance and he was carried the same evening to a hospital at Harper's Ferry. We marched almost immediately for Maryland, so I had no chance to see him. I think by this time he must be in some hospital further north.

I will take care of his clothing and perhaps there is a chance to dispose of it as he or you may wish. He is the first of our Hartford party who has met with any serious mishap. When he was wounded, our ...

... little battalion was under the sharpest fire we have ever experienced. We were under no cover and opposed by Gen. Early's Corps of infantry, they of course having the advantage of mounted men -- they being in the woods besides outnumbering us 30 to 1. Hoping Charlie's wound will not prove dangerous.

I remain 
Yours respectfully
Henry J. Appleby


18th Connecticut chaplain W.C. Walker's condolence letter to Greenleaf's parents dated Aug. 27, 1864.

Connecticut Historical Society collection
... he died yesterday Friday the 26th inst about 5 o'clock PM. His "great fortune has not always lasted," but he was a good soldier and now sleeps in honor in a soldier's grave, and must be received among the heros of this age, who stood by the flag of their country to the last and nobly fought its battles. Your loss is your country's loss too. ...


Charles Greenleaf pension file documents, newspaper clipping of letter to his parents about battle events in Shenandoah Valley near Strasburg, Virginia, May 26, 1863, National Archives and Records Service, Washington.

Greenleaf pension file, letter to parents, December 14, 1862, National Archives

Greenleaf letters, Civil War Manuscripts Project, Civil War Box II, Connecticut Historical Society, Hartford, Conn.

Lt. Henry Appleby letter to Greenleaf’s parents, August 27, 1864, Civil War Manuscripts Collection, Box II, CHS.

Chaplain W.C. Walker condolence letter to Charles Greenleaf parents, August 27, 1864, CHS

Hartford Daily Courant, September 20, 1864.


  1. Illustrative of how sad things could be during the war. Thanks for all your posts, Mr. Banks.

  2. Great story John, a must read. My Second Great Grand Uncle James Osborne, was in Company A, 2nd Ct. Heavy Artillery.

  3. Thanks for the kind words, Seward. You might be interested in my book, "Hidden History of Connecticut Union Soldiers." Lots more stories just like that. (Commerical is over now. :))

  4. I love these stories, John, because they take something overwhelmingly, humongously big and bring it to the individual, living persons who participated in it.