It's a good thing he knew the detour.
Daughters of the American Revolution
It was the evening of June 3, 1781– a Sunday– and war was on its way to Charlottesville.
Nearly forty miles to the east, at Cuckoo Tavern, John Jouett Jr. had finished dinner and gone outside to catch a few winks. Because of the oppressive late spring heat and the food and drink sitting heavily in his gut, “Jack,” as his friends called him, was soon fast asleep despite the revelry droning on in the background. Jouett was curled up under a great elm near the tavern’s picket fence, the only thing separating him from the county road.
A couple of hours before midnight, he was startled awake. Although Jouett was a strapping figure and an excellent horseman, the sight he saw as he peered into the moonlight toward the steadily approaching clatter had to be absolutely terrifying: a 250-man raiding party filling the dusty roadway for about 200 yards. At the head trotted the green-jacketed horsemen whose very name had grown infamous: the British Legion.
They were dragoons– horsemen armed and drilled to also fight dismounted— who were crown loyalists from New Jersey, Philadelphia, and New York City. A year earlier at the Battle of Waxhaws in South Carolina, these same cavalrymen– hardened Americans who had sworn allegiance to King George– had hacked their way through Virginia Continentals attempting to surrender. With sabers slashing, the Legion massacred dozens of patriots. Jouett would have heard the stories.
A ruthless leader
Bobbing alongside the vanguard that night was the Legion’s leader, Lieutenant Colonol Banastre Tarleton, a 26-year-old Liverpudlian who had risen in the ranks thanks to his fast riding, hard fighting, and ruthlessly aggressive nature. To the British, wrote historian Winthrop Sargent, Tarleton was “a capital horseman, the very model of a partisan leader.” To the Americans, however, he was the “Green Dragoon” or “Bloody Ban,” the commander– and, as it turned out, the butcher– at the massacre at Waxhaws.
“Tarleton’s Quarter!” had become a patriot rallying cry; it meant death to enemy troops with their hands in the air.
The road through Cuckoo (then, as now, just a tiny village in Louisa County), ran northwesterly to Louisa Court House, then onward to the gap in the Southwest Mountains at Pantops, a distance of about 38 miles. Just beyond sat the previously unimportant town of Charlottesville.
About three weeks earlier, however, the patriots had lost Richmond, so Charlottesville became the temporary state capital with the entire government— both houses of the legislature and Governor Thomas Jefferson– ensconced in Jefferson's hometown in the foothills. Jouett's father, John Jouett Sr., was the proprietor of Charlottesville’s Swan Tavern, just across from the courthouse, and at that very moment, no doubt, a number of the unsuspecting assemblymen were sampling the fare at Swan Tavern.
Inflamed by the sight of the enemy passing by him at Cuckoo Tavern, Jack Jouett’s thoughts must have raced. He would have instantly surmised Tarleton’s destination. But could he beat them to Charlottesville to sound the alarm? How could he get around them? Was his horse up to the challenge of such a long and treacherous ride?
Understanding the dire circumstances, Jouett quickly determined to risk his life in an attempt to thwart one of his country’s most fear and despised, enemy commanders.
Unlike the legendary “Midnight Ride” of Paul Revere— much celebrated in poetry, paintings, and even U.S. postage stamps— Jack Jouett’s overnight race from Cuckoo to Charlottesville remains relatively obscure. Perhaps it’s because Jouett, unlike Revere, was not already wealthy or famous when he undertook his heroic feat. And perhaps it’s because Jouett sought his post-war fortune out on the frontier, away from the centers of population and publicity.
Whatever the reason, the Central Virginian’s desperate dash, under the light of scrutiny, far outshines the Bostonian’s. Revere rode 15 miles on well-traveled Massachusetts roads, while Jouett rode at least 40 through the Virginia frontier. Moreover, the stakes in Virginia were higher. The state’s civil leadership, in its entirety, was seemingly Tarleton’s for the taking.
The war comes to Virginia
In 1781, the American Revolution was in its seventh spring, and things were not going well. Remarkably, the Old Dominion, supposedly the country’s most populous– and arguably its most powerful– state, had buckled quickly under the enemy’s blows with the entire administration skeddadling like a flock of frightened geese. How had the situation gotten so grim?
The tide had begun turning on December 30, 1780 when traitor Benedict Arnold— now an enemy general— had sailed up the James River with 1,800 men aboard 27 British warships. With the new capital at Richmond, with its military supplies and tobacco-packed warehouses, the obvious target, the last six months of Jefferson’s second one-year gubernatorial term were about to get ugly.
“When the general panic set in,” wrote historian John E. Selby, “the governor fled from the city with his family in the early morning hours of January 5.” Arnold captured the city that afternoon.
Two weeks later, after much burning and looting at Richmond and elsewhere along the James, Arnold sailed downstream to Portsmouth to dig in. Meanwhile, all across Virginia, county lieutenants desperately attempted to muster their militiamen, but too few turned out.
In April, a British fleet landed over 2,000 reinforcements at Portsmouth, and over the course of that month, the British launched several raids and actions fought all along the James— including a one-sided naval contest located between Richmond and Petersburg at a place called Osborne’s Landing. There, on April 27, the entire Virginia navy was lost, including—perhaps prophetically— a warship called Jefferson.
When the British again advanced against Richmond on the last day of April, this time they encountered French-born Major General Marquis de Lafayette at the head of 900 northern Continentals dispatched from George Washington’s army. The capital was rescued at the eleventh hour.
For the next month, this Lafayette-led force— augmented by some 1,500 untested militiamen— was the largest the Old Dominion could muster, but soon the 24-year-old Frenchman was greatly outnumbered.
The new British leader, General Charles Lord Cornwallis, had marched into Virginia from North Carolina with 1,500 additional British soldiers, and another 1,500 arrived by sea. Cornwallis was an experienced and aggressive officer with a consolidated British field army of about 7,200 veterans.
After remaining relatively unscathed for the war's first six years, Virginia had become the war’s most active theater.
"To frustrate these intentions"
“Cornwallis was not an aristocratic dilettante,” says Andrew O’Shaughnessy, director of the International Center for Jefferson Studies. “He was a real military professional. He was also a gambler, someone willing to take major risks. He essentially wanted to make Virginia collapse.”
Frustrated at his inability to ensnare Lafayette— whom Cornwallis called the “aspiring boy”— the 43-year-old Britisher decided instead to raid Virginia’s interior. Knowing that the governor and the relocated legislature would soon call out more state troops, Cornwallis ordered Tarleton— the brutal cavalryman— “to frustrate these intentions, and to distress the Americans, by breaking up the assembly.”
It was May 10, 1781 when the Virginia legislature determined to quit the state capital and reconvene in Charlottesville, beyond the Southwest Mountains.
Early on June 3, Lieutenant Colonel Tarleton set out from Hanover Court House, north of Richmond, with 180 dragoons from his own Legion and 70 mounted infantrymen from the 23rd Regiment, the Royal Welsh Fusiliers. These improvised horsemen, foot soldiers atop horseflesh stolen from the Virginia countryside, rode with light muskets slung across their red tunics.
At the time, an average horseman traveling unchallenging terrain could expect to cover 30 miles in a day. Tarleton had something much bolder in mind. As he later wrote, he planned “a march of seventy miles in twenty-four hours.”
Because the weather was unusually hot, however, the going was slow, and Tarleton’s column spent most of the first day to reach Cuckoo Tavern, a distance of about 30 miles. In order to bag his game, however, Tarleton was pushing his men to cover more.
It was about two hours before midnight when Jouett awakened to see the enemy raiders trotting past Cuckoo Tavern.
Jouett quickly donned his riding boots, “scarlet coat, and military hat and plume,” wrote Jefferson biographer Henry S. Randall. His bay mare Sally— which another historian called “the fleetest steed in seven counties," was nearby in the tavern’s paddock.
It would have been much easier to go back to sleep and hope that someone else could save Virginia’s government. Jouett knew, however, that his knowledge of the wilderness trails was unsurpassed. Providence could not have selected a better messenger.
A history in taverns
Born in Albemarle County on December 7, 1754, the 26-year-old Jouett has been widely described as intelligent and resourceful. He was also a strapping young fellow, according to Joel Meador, executive director of the Jack Jouett House in Versailles, Kentucky.
“He stood 6 feet 4 inches tall, and weighed about 220 pounds.” Unfortunately, little is known of his early days. “He was the son of a tavern owner,” says Meador.
Indeed, the running of wayside taverns— a lucrative business in the days when friendly stopping-places were few— seems to have been in the Jouett family blood. In 1742, Jack’s grandfather, Matthew Jouett, had opened an “ordinary” in his house near the present-day town of Louisa. Matthew’s son—John Jouett Sr., Jack’s father— had once been the owner of Cuckoo Tavern itself. After selling that establishment in 1773, Jouett Senior, wrote Edgar Woods (Albemarle’s first historian), purchased “one hundred acres adjoining [Charlottesville] on the east and north, and at that time most likely erected the Swan Tavern, of famous memory.” During the Revolution Jack Senior acted as a commissary, wrote historian Virginius Dabney, selling “considerable beef and other needed supplies... to the quartermasters of the Continental Army.”
The standard story— that Jack, as wrote Dabney, “was a captain in the Virginia militia, as were his three brothers” does not hold up under examination. A search of the state’s militia records revealed no Captain John Jouett. Instead, one of the early accounts—Randall’s 1858 biography of Jefferson—referred to Jack as a “showy gentleman” who “was no officer,” but had “an eccentric custom” of wearing military-style getup.
Patriotism, evidently, was also a dominant trait in this French Huguenot family. With two Jouetts serving in the Virginia Continental Line (the regular army at the time)—older brother Matthew in the 7th Virginia (mortally wounded at the 1777 Battle of Brandywine), and Robert in Col. James Wood’s 12th Virginia– Jack and his father may have felt compelled to make a political statement of their own. In June of 1779 both signed the curious Albemarle “Declaration of Independence” which stated in part that: “we renounce… all Allegiance to George the third… [and] will be faithfull & bear True Allegiance to… Virginia as a free & independent state.”
An abandoned road
Freedom and independence were certainly at stake as Jouett began sorting his thoughts on that moonlit night. Jouett had no way of knowing if anyone else was was to get ahead of Tarleton’s troopers. If he was indeed acting alone, the Old Dominion’s fate was resting on his skills, the evening’s visibility, and Sally's speed.
Cantering along Mountain Road, the main highway, at a safe distance behind Tarleton’s column, Jouett must have realized he had to get around them to beat them to Monticello and Charlottesville. Finding a detour might be an impossible proposition on a dark night. Fortunately, this one had a nearly full moon.
Moving cautiously once he neared Louisa Courthouse, Jouett must have caught a glimpse of polished buttons and metal-sheathed sabers, as historian Tapp wrote, that in the moonlight he "could see dimly the dragoons moving about.” The raiders had stopped to water their horses and refresh themselves, and Tarleton later wrote that he “halted at eleven near Louisa court house, and remained on a plentiful plantation till two o’clock.”
In the dense wilderness that covered Virginia in the 18th century, well-maintained roads were in short supply. While Mountain Road was blocked by the Loyalist forces, Jouett knew that to its south, across the South Anna River, was Three Notch’d Road leading all the way from Richmond (where it's called Three Chopt Road) to the Shenandoah. To best outstrip Tarleton, therefore, Jouett had to find a way southwestward, toward the road whose famous signposts— trees bearing three hatchet chops, like chevrons— would thereafter guide him to Charlottesville.
But how? Somewhere nearby was the answer: an old logging trail that had supplied the logs for the court house.
"He knew the trail well," wrote historian Tapp, "having hunted along it.”
So off he and Sally went.
“His progress was greatly impeded by matted undergrowth, tangled brush, overhanging vines and gullies,” wrote Virginius Dabney. “[H]is face was cruelly lashed by tree limbs as he rode forward, and scars said to have remained the rest of his life were the result of lacerations sustained from these low hanging branches."
Drenched with sweat, Jouett splashed through the South Anna somewhere south of Louisa Court House. Perhaps he stopped briefly to water Sally, and perhaps he even washed off her flanks, now covered with scratches. Soon he was back in the saddle.
“He could judge by the position of the moon that the night was far spent, causing him to travel faster,” wrote Tapp, “He was determined to beat Tarleton or die in the effort.”
Within a few miles, Jouett turned on to Old Mountain Road and then onto Three Notch’d. Heading west along the latter well-marked byway, Jouett spurred Sally to even greater efforts. He still had miles to go, and Tarleton’s force was still on the move.
The Affair of Carter's Mountain
Before daybreak, the marauders had detained “some of the principal gentlemen of Virginia” and captured a member of the Continental Congress, Frances Kinloch, and burned 12 wagons carrying weapons and clothing for the Continental Army.
At Castle Hill, the Keswick-area estate of Dr. Thomas Walker— discoverer of the Cumberland Gap into Kentucky— the British cavalrymen rested for half an hour. This brief stopover has been the subject of numerous tall tales, all involving an elaborate, delaying breakfast. None, however, should be believed, because Tarleton would not have fallen for such a ruse. He was in a hurry.
Meanwhile, Jouett and Sally were crossing the Rivanna River at the village of Milton and then ascending Monticello Mountain three weary miles later. It was 4:30am.
How Jouett must have appeared upon arrival is lost to history. What is recorded is that Jefferson's guests included members of the General Assembly including the speakers of both houses. Jefferson would later write that the legislators “breakfasted at leisure” before proceeding to Charlottesville.
Legend has it that as Jouett remounted to spread the alarm Jefferson offered up a glass of fortifying Madeira.
Jefferson himself, however, remained unhurried. Perhaps it was because his ill-fated governorship had ended two days earlier. (This meant, of course, that at the moment Virginia had no chief executive.)
After sending off his family and carefully organizing his papers, Jefferson was warned again of the British approach, as he could see– via telescope– soldiers arriving in Charlottesville. Finally, he galloped up the adjoining wooded slope where he'd sent his family. Ascending nearby Carter's Mountain, Jefferson was mere minutes ahead of the first loyalist dragoons under a detachment led by Captain Kenneth McLeod.
Two of Jefferson’s slaves, Martin and Caesar, "were engaged in secreting plate and other valuables under the [planked] floor of the front portico, when McLeod’s party arrived," according to Randall. Just as the last piece of silver was handed down to Caesar “in the cavity,” Martin either heard the hoofbeats, or saw the loyalists through the trees, “and down went the plank, shutting Caesar into the dark hole below.” There Caesar would remain “without light or food” until McLeod’s troopers departed, many hours later.
Although Jefferson quickly rejoined his family at the nearby estate of Blenheim, he later referred to this extremely troubling episode— the so-called “Affair of Carter’s Mountain”— as the nadir of his political career.
Daniel Boone and Jouett
Little Charlottesville, in the meantime, was a blur of activity. Warned by Jouett, the assemblymen hastily convened and decided to meet again three days later in Staunton, forty miles further west. Then they scattered.
After dispatching McLeod to Monticello, Tarleton had charged through Moore's Creek and overpowered a small militia force at Secretary’s Ford, eventually site of the Woolen Mills, and then thundered onto the courthouse square. Most of the flock, of course, had flown.
“Seven members of the assembly were secured,” wrote Tarleton, neglecting to list their names, “and several officers and men were killed, wounded, or taken.” During their one-day stay, the British discovered “a great quantity of stores,” and destroyed “one thousand firelocks... [u]pwards of four hundred barrels of powder” and “[s]everal hogsheads of tobacco.”
Jack Jouett’s later activities that morning are difficult to sort out.
Historian Randall wrote that Brigadier General Edward Stevens— wounded in battle and now serving in the legislature— was able to elude the British dragoons because he was dressed as a Virginia farmer and mounted on a shabby horse. “Mr. Jouett,” however, thanks to his ersatz military attire, “was more attractive game.” So the enemy took off after him instead. “After [Jouett] had coquetted with his pursuers long enough, he gave his fleet horse the spur, and speedily he was out of sight.”
Another story revolves around Daniel Boone. Representing the massive western Virginia county of Kentucky, the famous frontiersman was among the legislators in Charlottesville that day. As noted in My Father, Daniel Boone, youngest son Nathan Boone related the following 70 years later:
“[W]hen Jack Jouett gave notice of Tarleton’s approach, my Father… remained, loading up on wagons the public records. [W]hen they were overtaken by the British, questioned hastily, and dismissed… [Jouett] called out, ‘Wait a minute, Captain Boone, and I’ll go with you.’” An enemy officer then asked, “Ah, is he a captain?” and took Boone into custody. Conveyed to the British camp east of town, and held overnight in a coal house, the legendary frontiersman was reportedly interrogated by Tarleton and released.
The two stories are difficult to square, as they seem contradictory. One has Jouett racing away from Charlottesville because of his ostentatious military garb. The other has him completely overlooked by the British— despite shooting off his mouth at the courthouse. Did either of these events take place? We’ll probably never know.
What we do know is that on June 15, 1781, just two weeks later, the assemblymen resolved that Jouett should receive “an elegant sword and pair of pistols as a memorial of the high sense which the General Assembly entertain of his activity and enterprise.”
After all, thanks to Jouett’s ride, four signers of the Declaration of Independence escaped capture: Thomas Jefferson, Benjamin Harrison, Thomas Nelson Jr. and Richard Henry Lee. A “Who’s Who” of Virginia history, this extraordinary list comprises a future president (Jefferson), the father of another future president (Harrison, whose son William Henry was elected in 1840), and the man who next became Virginia’s governor (Nelson). Patrick Henry was also among the escapees, as was the father of John Tyler, Jr., who followed William Henry Harrison into the White House.
Jack Jouett got the pistols two years later, but his receipt of the sword was delayed twenty years. By that time, he’d made quite a name for himself out on the frontier.
Jouett had managed Swan Tavern for a spell, but in 1781, like thousands of other Virginians, he lit out for Kentucky. Two years later, he married Sallie Robards, a relative of Andrew Jackson’s, and the couple had 12 children. In 1787, and again in 1790, according to historian Lewis Collins, Jouett represented his region of Kentucky in the Virginia General Assembly. The year Kentucky gained statehood, 1792, Jouett was elected to the new state legislature. Jouett was an agricultural leader as well; he imported livestock in large numbers and thus helped the Bluegrass State achieve its cattle- and horse-breeding fame.
In Kentucky, Jack Jouett is remembered as a high liver, a man full of humor and fun. Remarkable for his hospitality, Jouett, became a friend of Henry Clay and Andrew Jackson, "indeed of all the great men of early Kentucky," Collins wrote.
Jack Jouett died at Peeled Oak, his Bath County, Kentucky farm, on February 21, 1822. He was buried in the nearby family cemetery, where unfortunately, says Meador of the Jack Jouett House, "all the stones have been lost." Somehow it seems fitting that the Central Virginia patriot whose early life and heroic deed have been mostly lost to history, now lies lost out on the Kentucky frontier.
“Even in death,” says Meador, “he’s still very much a mystery.”
Rick Britton writes about history and makes maps for many publications, including books he has written. His other Hook cover story was "Unhappy Grandpa," a 2008 piece about the twilight years of Thomas Jefferson.