On the 4th of July, 1862, 900 cavalrymen from Confederate General Kirby Smith's army in east Tennessee, headed west out of Knoxville under the command of Colonel John Hunt Morgan.  Almost all of the men of the 2nd Kentucky Confederate Cavalry were mounted on American Saddlebreds.

Two days later a similar force of Tennessee cavalrymen from Smith's army, led by Colonel Nathan Bedford Forest, left Chattanooga to wreak havoc in Middle Tennessee.

Company D of the 2nd Kentucky was commanded by 21-year-old Captain John B. Castleman.  These raiders were on their way back home to Kentucky to gather recruits, horses, supplies, and to harass the occupying Federal forces in preparation for a massive Confederate invasion a few weeks later.

They went to Sparta, Tennessee, then 90 miles northeast to Tompkinsville, Kentucky, where they captured an entire battalion, 400 men of the 9th Pennsylvania Cavalry.  They hit the Louisville & Nashville Railroad 30 miles north of Tompkinsville.  Wherever they went they were welcomed by Confederate sympathizers, Glasgow, Springfield, Harrodsburg, Versailles, and Midway.

Morgan sent one company all the way to the Ohio River northeast of Louisville to panic Federal troops and civilian Union sympathizers.

President Abraham Lincoln wired his Department Commander General Henry Halleck, "They are having a stampede in Kentucky.  Please look into it."

Texas cavalrymen in Morgan's command, led by Richard Gano, captured Georgetown, on July 13.  The main force arrived there July 15, and they rested and recruited.  Morgan's recruiting efforts were successful, but he was overly optimistic.  After the Confederate invasion of Kentucky in August, General Kirby Smith wrote, "The Kentuckians are slow and backward in rallying to our standard.  Their hearts are evidently with us, but their bluegrass and fat cattle are against us."

The primary objective of Morgan's first raid was Cynthiana, located on the main line of the Kentucky Central Railroad between Lexington and Cincinnati.  The town, which was defended by Union forces, was a supply base and had large U.S. Government corrals for horses going into the army as cavalry mounts and to pull artillery pieces and supply wagons.  At Cynthiana, Col. Morgan hoped to tear up the railroad, to disrupt Federal communications, and to capture horses.

As the troopers, including many new recruits, were formed up on the Georgetown square the morning of July, 18 1862, Col. Morgan called Captain Castleman front and center and explained the situation to him.  The Confederates were going to Cynthiana, then to Paris, and on to Winchester.

There was a large Federal garrison in Lexington, and Morgan was concerned that Cynthiana could be reinforced.  He ordered Captain Castleman to take Company D and menace the Federals, try to destroy communications between Lexington and Cynthiana, and to rejoin the regiment two days later at Winchester, Kentucky.

While Col. Morgan and the main force headed east and north, 83 horsemen rode south out of Georgetown toward Lexington.  When Company D reached the intersection of Iron Works Pike and Georgetown Road, Castleman sent a nine-man patrol toward Lexington to attack Federal picket posts guarding the city.  The patrol accomplished its mission. deceiving Lexington's defenders into thinking an attack was coming down Georgetown Road.   The horsemen returned to Company D after having made the 14-mile round trip in an hour.

The Confederates rested their horses at Donarail. The railroad station near Iron Works and Georgetown Road.  From there, Castleman could see the mansion of James D. Duke, a famous horseman and uncle of Col. Morgan's second-in-command, Lt. Col. Basil W. Duke.

Basil Duke had been raised by his aunt and uncle, and John Castleman recalled the first meeting with his comrade in arms.  Young Basil and John went to the spring house and took a toy cannon down from the loft.  They charged it with powder and fired at calves grazing nearby, but did not injure them.

The realities of the situation roused the young commander from his reverie.  The troopers were called to order by Sergeant J. Lawrence Jones, later a great owner and exhibitor of show horses.  They turned their Saddle Horses on to Iron Works, then a dirt road, and proceeded east.  They passed what is today the entrance to the Kentucky Horse Park on their left, the entrance to Spindletop Hall on the right.

About 11 a.m. they halted 800 yards away from the intersection of Iron Works and Newtown Pike, which was then called Taylor's Crossroads.  Three neighborhood boys, including young George A. Castleman, warned the Confederates, who were concealed by a rise of ground, that about 2,000 Union cavalry commanded by Colonel Leonidas Metcalf were moving slowly out of Lexington, north on Newtown Pike.  They were accompanied by a battery of artillery commanded by Castleman's friend U.S. Captain Henry T. Duncan, Jr., whose father had bred the great stallion Grey Eagle.

The gray riders advanced to within 300 yards before being seen by the Federal advance guard, which was already at the crossroads.  Some of the Yankees were dismounted when the Rebels charged.  They chased the Yanks south on Newtown Pike.  The head of the main Federal column had halted about a half mile out of Lexington, and the frightened patrol ran through the head of the column with Castleman and his troopers hot on their heels.  Castleman later said, "We stampeded Metcalf's brigade!"

Company D then quickly withdrew, galloping back up Newtown Pike until they again reached Iron Works.  Several Federals had been killed and wounded, but there were no Confederate casualties.

A short distance from Taylor's Crossroads, east of Newtown and north of Iron Works, is Mt. Horeb Presbyterian Church and behind the church is the mansion at Castleton Farm where John B. Castleman was born.  The Castleton property lay on both sides of Iron Works Pike.

The Confederates watered their horses in the shallow Taylor's pond and let them graze while holding the bridle reins.  Castleman sent out scouts to watch the enemy.  He was determined to hold Metcalf at bay a while longer because he didn't know what was happening to Morgan at Cynthiana.

At 2 p.m., the pickets reported that the Federals were again on the move, with about 250 horsemen and artillery coming up Newtown Pike.

Fence rails along the roads had been removed, and Company D retired behind Mt. Horeb Church where the men and horses could not be seen.  Captain Castleman sent seven troopers on foot to conceal themselves along Iron Works and ordered them to fire a single, well aimed volley when the cavalry charged.  The second platoon would have to charge through a shallow portion of Taylor's Pond.

The Rebels waited nervously in the church graveyard, and Castleman later wrote that his own horse was astride his father's grave.  When the slowly advancing Yanks reached a point directly opposite the Confederates, the Rebs charged from either side of the church.

The sharpshooters emptied some Yankee saddles and again the Federals turned tail toward Lexington.  What the Confederates did not know was that Capt. Duncan had two 20-pound Parrott guns loaded with canister waiting for them.  There were stone walls along both sides of Newtown Pike which in effect acted like a funnel.

Duncan could not give the order to fire until the retreating Federals had cleared the way, and Col. Metcalf said to him, "I do not wish to kill our Kentucky boys in Morgan's command, and it would be like murder to fire on them when crowded in the turnpike.  I want to take them as prisoners."

Suddenly, the Rebels turned and rode back up Newtown Pike and disappeared behind the church.  The Federal artillery opened up, thinking the three boys who were watching the whole affair from a wooded pasture near Taylor's Crossroads were more of Morgan's men.  The youngsters drove cattle and horses in the pasture out of danger before they were "captured" by the Federals and taken to the Lexington jail where they were kept for a short time.

Morgan accomplished his mission capturing Cynthiana and then Paris.  On the way to Winchester, Company D cut down telegraph poles and destroyed two small railroad bridges.  Castleman's men arrived at Winchester before Morgan's main force but captured and held the town until Col. Morgan came the next day.

The raid had accomplished what it set out to do and made John Hunt Morgan famous and gave young officers like Captain John B. Castleman invaluable experience for the hardships they would endure for the next four years.  A few weeks later, Morgan and his men would again range into the Bluegrass from their camps in Tennessee, providing the superiority of their horses, American Saddlebreds.

This article was written by Lynn Weatherman
copied from the American Saddlebred Magazine May/June 1991