Because the heat was oppressive, and perhaps because the dinner and drink sat heavy in his gut, John Jouett Jr. curled up beneath the great elm in the yard at Cuckoo Tavern to catch a few winks. Despite the revelry droning on in the background, “Jack,” as his friends called him, was soon fast asleep. It was the moonlit evening of June 3, 1781—a Sunday. The American Revolution was in its seventh spring.
Startled awake at 10:00 p.m., Jouett peered into the moonlight toward the steadily approaching clatter. The sight was absolutely terrifying; a 250-man British raiding party—dragoons and mounted infantrymen—that filled the dusty roadway for 200 yards. At the head trotted green-jacketed horsemen whose very name had grown infamous. They were the British Legion, loyalists from New Jersey, Philadelphia, and New York City; hardened Americans who had sworn allegiance to King George. At the Waxhaws in May of 1780, these dragoons, sabers slashing, had hacked their way through Virginia Continentals attempting to surrender. Dozens were massacred.
Bobbing alongside the vanguard was the Legion’s commander, Lieut. Col. Banastre Tarleton, a twenty-six-year-old Liverpudlian who had risen in the ranks thanks to fast riding, hard fighting, and a ruthlessly aggressive nature. To the Americans this “Green Dragoon” was a butcher—“Bloody Ban.” And since the Waxhaws “Tarleton’s Quarter!” had become a patriot rallying cry; it meant death to enemy troops with their hands in the air. To the British, however, Banastre Tarleton was “a capital horseman, the very model of a partisan leader.”
Jouett instantly surmised Tarleton’s destination. The road fronting Cuckoo ran northwesterly to Louisa Court House, then onward to the gap in the Southwest Mountains at Pantops (a distance of about forty miles). Just beyond sat the previously unimportant backwater town of Charlottesville. Now, however, Charlottesville was serving as the temporary state capital because three weeks earlier, at the approach of the enemy, the entire government—both houses of the legislature and Governor Thomas Jefferson—had fled Richmond for points west. This Jack knew because his father, John Jouett Sr., was the proprietor of Charlottesville’s Swan Tavern, just across from the courthouse. At that very moment, no doubt, a number of the unsuspecting assemblymen were sampling Jouett Senior’s fare.
Understanding the dire circumstances—Virginia’s civil leadership, in its entirety, was seemingly Tarleton’s for the taking—Jack Jouett mounted his horse and set off for Charlottesville. He was one rider, alone, on a mission to thwart one of his country’s most despised, and feared, enemy commanders. The Revolutionary War had finally come to Virginia’s backcountry Piedmont.
Unlike the legendary “Midnight Ride” of Bostonian 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 famous or well-to-do when he performed his heroic feat. And perhaps it’s because Jack Jouett after the war sought his fortune out on the newspaper-sparse frontier, away from the centers of population and publicity. Whatever the reason, however, the central Virginian’s desperate dash, under the light of scrutiny, far outshines Revere’s. Thanks to Jack Jouett’s 40-mile ride, four signers of the Declaration of Independence escaped capture. So did a future president, the father of another future president, and the state’s chief executive (among many others). What seems most remarkable is that the Old Dominion, supposedly the country’s most powerful state, had buckled so quickly under the enemy’s blows. And that the entire administration was skeddadling like a pack of frightened geese. For Revolutionary Virginia, this was the time that tried men’s souls.
How had the situation gotten so grim? Amazingly, for the war’s first six years, Virginia—by far the most populous state—remained relatively unscathed. That changed quickly during the first five months of 1781; coincidentally the last five months of Jefferson’s second one-year gubernatorial term. On December 30, 1780, the traitor Benedict Arnold—now an enemy general—sailed up the James River with 1,800 men aboard 27 British warships. The new capital at Richmond, with its military supplies and tobacco-packed warehouses, was the obvious target. “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, an action occasioning charges of cowardice that plagued him throughout his political career.” Arnold captured the city that afternoon. Two weeks later, after much burning and looting at Richmond and along the James, Arnold sailed downstream to Portsmouth and dug in. Meanwhile, all across Virginia, county lieutenants attempted to muster their militiamen. Too few turned out.
Two months later a British fleet landed over 2,000 reinforcements at Portsmouth. Over the course of April, the British launched a number of raids, and actions were fought all along the James—including a battle at Blandford, and a one-sided naval contest at Osborne’s. There, on the twenty-seventh, the entire Virginia navy was lost, including—perhaps prophetically—the Jefferson, which was scuttled. When the British again advanced against Richmond on April 30, the capital was rescued, at the eleventh hour, by Maj. Gen. Marquis de Lafayette at the head of 900 northern Continentals dispatched from George Washington’s army. For the next month this force—augmented by some 1,500 untested militiamen—was the largest the Old Dominion could muster. When Gen. Charles Lord Cornwallis marched into Virginia from North Carolina with 1,500 additional British soldiers, and another 1,500 arrived by sea, the twenty-four-year-old Lafayette was suddenly greatly outnumbered. Facing him was a consolidated British field army of about 7,200 veterans. And the new leader, Cornwallis, was an experienced and aggressive officer. In the course of but a few months, Virginia had become the war’s most active theater of operations.
“Cornwallis was not an aristocratic dilettante,” says Andrew O’Shaughnessy, Saunders Director of the Robert H. Smith 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.” Surprisingly, the Old Dominion seemed willing to acquiesce. On May 10, because of the deteriorating military situation, the Virginia legislature determined to quit the state capital and reconvene in Charlottesville, beyond the Southwest Mountains.
Lafayette also abandoned Richmond when Cornwallis advanced a few weeks later. Frustrated at his inability to ensnare Lafayette, the forty-three-year-old Britisher decided instead to raid into Virginia’s interior. Knowing that the governor and the legislature had fled to Charlottesville, and knowing that from that point they’d call out more state troops, Cornwallis ordered Tarleton—the brilliant and brutal cavalryman—“To frustrate these intentions, and to distress the Americans, by breaking up the assembly. . . .”
Early on June 3, Lieutenant Colonel Tarleton set out from Hanover Court House, north of Richmond, with 180 horsemen from his own Legion augmented by seventy mounted infantrymen from the 23rd Regiment, the Royal Welsh Fusiliers. These improvised horsemen, foot soldiers atop horseflesh stolen from the Virginia countryside, rode with their light muskets slung across their red tunics. Because the weather was exceedingly warm, the going was slow. Tarleton’s column, in fact, took up most of the first day to reach Cuckoo Tavern, a distance of about thirty miles.
Jack Jouett’s thoughts can only be imagined as he espied the enemy raiders. Disregarding his own safety, however, the Virginian was immediately concerned for his country, and his country’s government. Fortunately his bay mare Sally—“the fleetest steed in seven counties,” according to Hambleton Tapp—was nearby in the tavern’s paddock. Quickly donning his riding boots, scarlet jacket, and plumed military cap, Jouett was soon cantering down the highway at a safe distance behind Tarleton’s column. Somehow he had to beat them to Monticello and Charlottesville. It was a dangerous proposition, no doubt, and Jouett had no way of knowing if anyone else was similarly engaged on that moonlit night. If he was indeed acting alone, the Old Dominion’s fate was resting on the evening’s visibility, and Jouett’s knowledge of the wilderness trails. Providence could not have selected a better messenger.
Born in Albemarle County on December 7, 1754, the twenty-six-year-old Jack Jouett, Jr. has often been described as “intelligent, resourceful, daring and brave.” He was also a strapping young fellow, according to Joel Meador, executive director of the Jack Jouett House in Versailles, Kentucky: “He stood six feet four inches tall, and weighed about 220 pounds. He was the son of a tavern owner.” 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 present-day 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, 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 he acted as a commissary, selling “considerable beef and other needed supplies . . . to the quartermasters of the Continental Army.”
Patriotism, evidently, was also a dominant trait in this French Huguenot family, although the standard story—that Jack “was a captain in the Virginia militia, as were his three brothers,” Matthew, Robert, and Charles—does not hold up under examination. A search of the state’s militia records revealed no Capt. John Jouett. Instead, one of the earliest accounts referred to Jack as a “showy gentleman” who “was no officer,” but had “an eccentric custom” of wearing military-style getup. Two brothers, however, were captains in the Virginia Continental Line—older brother Matthew in the 7th Virginia Regiment (who was mortally wounded at Brandywine), and Robert in Col. James Wood’s 12th Virginia. With two Jouetts serving in the Continental Army, Jack and his father evidently felt compelled to make a political statement. 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. . . .”
Freedom and independence were certainly at stake as Jouett, an excellent horseman, trotted in the wake of Tarleton’s troopers. Moving cautiously once he neared the courthouse, Jouett, wrote Tapp, “could see dimly the dragoons moving about.” The raiders had halted to water their horses. Polished buttons, and especially metal-sheathed sabers, reflected under the bright moonlight. Tarleton wrote that he “halted at eleven near Louisa court house, and remained on a plentiful plantation till two o’clock.” The best road blocked, Jouett “turned Sally into an abandoned road by way of which the logs for the Court House had been brought. He knew the trail well, having hunted along it.”
In the eighteenth century, central Virginia was not a region crisscrossed by numerous well-maintained roads. The best trails running east-to-west through the dense wilderness, in fact, were that being used by the British, and to its south, across the South Anna River, the Three Notched Road leading from Richmond to the Shenandoah. To best outstrip Tarleton, therefore, Jouett headed southwestward, toward the trail whose famous signposts—trees bearing three hatchet chops, like chevrons—would thereafter guide him to Charlottesville. This meant traversing logging trails and seldom-used cow paths. “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 into 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,” wrote Tapp, “that the night was far spent, causing him to travel faster. . . . He was determined to beat Tarleton or die in the effort.” Within a few miles Jouett stumbled into Three Notched Road. Heading west along this well-marked byway, Jouett spurred Sally to even greater efforts. He still had twenty-five miles to go.
Tarleton’s force was on the move again at 2:00 a.m. Before daylight, the marauders captured and burned twelve wagons carrying weapons and clothing for the Continental Army. Just after daybreak, wrote Tarleton, “some of the principal gentlemen of Virginia, who had fled . . . to the mountains for security, were taken out of their beds.” At Castle Hill, the 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 involve an elaborate, delaying breakfast; none should be believed. Nearby a member of the Continental Congress, Frances Kinloch, was captured.
Crossing the Rivanna at Milton, Jouett ascended Monticello Mountain three weary miles later. It was 4:30, “a little before sunrise.” Alerted, Jefferson’s guests—members of the assembly plus the speakers of both houses—“breakfasted at leisure” then proceeded to Charlottesville. Legend has it that Jefferson offered up a glass of fortifying Madeira when Jouett remounted to spread the alarm. Jefferson, however, was 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 before he finally galloped up the adjoining wooded slope. He was mere minutes ahead of loyalist dragoons under Capt. Kenneth McLeod. Jefferson later referred to this extremely troubling episode—the so-called “Affair of Carter’s Mountain”—as the very nadir of his political career.
Little Charlottesville, in the meantime, was a blur of activity. Warned by Jouett, the assemblymen quickly convened and decided to meet again three days later in Staunton, forty miles further west. Then they scattered. After dispatching McLeod to Monticello, Tarleton charged through a small militia force at Secretary’s Ford, then thundered onto courthouse square “to apprehend, if possible, the governor and assembly.” 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 other activities that morning are difficult to sort out. Henry S. Randall wrote that Brig. Gen. Edward Stevens—wounded in battle and now serving in the legislature—was able to elude 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.”
Daniel Boone—representing the massive western county of Kentucky—was among the legislators in Charlottesville that day. Nathan Boone, Daniel’s youngest son, related the following seventy 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 said “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, they seem contradictory. One has Jouett completely overlooked by the British—despite shooting off his mouth—while the other has him racing away from Charlottesville because his military garb makes him more noticeable. Did either of these events take place? We’ll probably never know.
What we do know is this: 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. . . .” Jack Jouett got the pistols in 1783, 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, then, like thousands of other Virginians, he lit out for Kentucky in 1782. Two years later he married Sallie Robards (a relative of Andrew Jackson’s wife). The couple had twelve children. In 1787, and again in 1790, Jouett represented his region of Kentucky in the Virginia General Assembly. The year Kentucky gained statehood, 1792, Jouett was elected to represent Mercer County in the new state legislature. Three years later he represented Woodford County. 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 was “the associate and companion of Henry Clay and Andrew Jackson . . . indeed of all the great men of early Kentucky.” He was a man of note in his day. 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 historic site, “all the stones have been lost.” Somehow it seems fitting. Jack Jouett, the central Virginia patriot whose deed has been lost to history, now lays lost out on the Kentucky frontier. “Even in death,” explains Meador, “he’s still very much a mystery.”
 Hambleton Tapp, “Jouett’s Desperate Ride, The Lost Chapter of the American Revolution: Jack Jouett, Virginian, Kentuckian” University of Kentucky Magazine (Lexington, KY, ____), pg. 6. The accounts differ as to Jouett’s location when Tarleton rode past. Some say he was at the tavern, others place him at his father’s farm in Louisa County. It’s a tossup so I chose the one which seems the most provincial.
 Henry S. Randall, The Life of Thomas Jefferson (New York, 1858), pgs. 336–37. Randall claimed that much of his information had been gleaned from interviewing the descendants of the Jefferson/Randolph family.
 Randall, The Life of Thomas Jefferson, pg. 337. Perhaps young Jack was jealous of his brothers? Several accounts refer to his seemingly odd habit of wearing military getup. He would not have been described this way if he were an actual officer. Most likely, he was described once as a “captain,” and this was copied by other historians. Also, in Kentucky Jack applied for the pension owed his brother Matthew (for military service), not for his own.