The elder Jouett held a license to operate the Swan "ordinary" (tavern) in Albemarle County, Virginia.

His paternal ancestors were an old Norman aristocratic family from Touraine, directly descended from Matthieu de Jouhet, Master of the Horse to Louis XIII of France,[3][4][5] Lord of Leveignac, and a lieutenant in the Marshalsea of Limousin.

[7] Jack Jouett became a captain in the 16th Regiment of the Virginia militia during the American Revolutionary War, during which all three of his brothers also served.

A physically imposing, as well as muscular and handsome man, Jack stood 6 ft 4 in (1.93 m) tall and weighed 220 lb (100 kg).

[8] His father, John Jouett Sr., was also very active in the revolutionary cause in Albemarle County, Virginia, and supplied the militia with meat for its rations, as well as supporting his sons' service.

Legislators targeted for capture included Patrick Henry, Richard Henry Lee, Thomas Nelson Jr., and Benjamin Harrison V.[12] On June 3, Tarleton left Cornwallis's camp on the North Anna River[10] with 180 cavalrymen and 70 mounted infantry of the Royal Welsh Fusiliers.

Tarleton marched his force covertly and planned to cover the last 70 miles to Charlottesville in 24 hours, a fast maneuver intended to catch the politicians completely unaware.

[12] His orders from Cornwallis, however, were to first destroy the military supplies at Scott's Landing before General Lafayette and his men, marching from Baltimore, Maryland, could interfere.

With the British cavalry on the main highway, Jouett had to take the rough backwoods trails to the overgrown Old Mountain Road, likely traveling only with the light of the full moon.

Supposedly, Dr. Walker prepared an elaborate breakfast (including alcohol), for Tarleton in order to allow more time for Jefferson and the legislature to get warning of the cavalry.

Tarleton's account says he did pause at Castle Hill for a half-hour rest, but the story of Walker's ploy is probably apocryphal.

Jefferson did not rush, although he sent his wife and daughters to Enniscorthy, his friend John Coles' plantation about 14 miles (23 km) away.

When Captain Christopher Hudson rode to Monticello to warn of the imminent British arrival, Jefferson continued his preparations, but sent a horse outside his estate for a quick escape.

[9] One enslaved Monticello family's oral history claims Jefferson "hid in the hollow of an old tree" on nearby Carter's Mountain.

[15] Other traditions claim Jefferson spent two weeks at the home of Thomas Farrar, and some time in a cliff-cave near Scotts's Landing about a mile downstream from his brother Randolph's plantation, "Snowden", while Tarleton commandeered Jefferson's "Elk Hill" plantation in Goochland County.

[18] Jouett was wearing an ornate military costume with a scarlet coat and a plumed hat, and Stevens was dressed in shoddy clothing.

[19] In 1782, Jouett moved across the Appalachian Mountains to Kentucky County, where veterans received land claims for their service.

A family story claims that, on his journey to Kentucky, Jouett heard a woman's screams coming from a house.

Lincoln County voters elected Jouett as their representative in the Virginia House of Delegates (alongside Benjamin Logan).

This house was built in the style of the traditional hall and parlor plan, and was erected during the mid-Federal period, five years after Kentucky statehood, and features five rooms—three downstairs and two half-story bedrooms upstairs.

"[9] Matthew Jouett had attended Transylvania University and read law with George M. Bibb, and his father approved his enlisting in the 3rd Mountain Regiment of the Kentucky Volunteers during the War of 1812.

The regiment's payroll was lost during the Battle of the River Raisin and it is said Matthew became a portrait painter to earn the money back.

Local Bath County historians such as John A. Richards have concluded that Jack did die while at his daughter's home (Elizabeth Haden or Polly Stockton) but he was buried at the Tanyard Graveyard, a place where many Revolutionary War Veterans of the area were known to have been laid to rest, two miles northeast of Jack's Woodford Farm.

[34] In an attempt to promote Jouett's memory, the Charlottesville Daily Press published the following poem on October 26, 1909: Hearken good people: awhile abide And hear of stout Jack Jouetts ride; How he rushed his steed, nor stopped nor stayed Till he warned the people of Tarleton's raid.

His parting steed he spurred, In haste to carry the warning To that greatest statesman of any age, The Immortal Monticello Sage.

[citation needed] The Three Notch'd Brewing Company in Charlottesville named their flagship India Pale Ale "40-mile" to honor Jouett's ride.