Founding, colonial era
Caroline County was established in the British Colony of Virginia in 1728 from Essex, King and Queen, and King William counties. It was named for Caroline of Ansbach, the wife of King George II of Great Britain.
During the Colonial Period, Caroline County was the birthplace of Thoroughbred horse racing in North America. Arabian horses were imported from England to provide the basis for American breeding stock.
Patriot Edmund Pendleton played a large role in the Virginia Resolution for Independence (1775). Caroline native John Penn was a signer of the Declaration of Independence, albeit as a delegate from North Carolina.
Explorers William Clark and his slave York were members of the Lewis and Clark Expedition (1803–1805), and William's older brother, General George Rogers Clark--conqueror of the old Northwest Territory and Revolutionary War hero. Both were born near what is now Ladysmith.
In 1847, after being a member of the first graduating class of Virginia Military Institute (VMI), William "Little Billy" Mahone (1826–1895) of Southampton County began teaching at Rappahannock Academy in Caroline County. He was to become prominent as a railroad builder and developer, Confederate General, leader of Virginia's short-lived Readjuster Party, and a United States Senator.
On May 10, 1863, Confederate Lieutenant General Thomas "Stonewall" Jackson died of complications from pneumonia at the Chandler plantation in Guinea Station (also known as Guiney's Station), in the unincorporated Caroline County community of Woodford. The Chandler residence is now known as the "Jackson Shrine."
During Union General Ulysses S. Grant's Overland Campaign, Confederate troops under General George E. Pickett fought Union troops near Milford. Just as the Civil War was concluding in April 1865, President Lincoln was assassinated in Washington, DC as part of a conspiracy to kill the leaders of the United States. As the conspirators fled, a manhunt was launched. After 10 days, in the wee hours of April 26, federal troops tracked down John Wilkes Booth, Lincoln's assassin, and fellow conspirator David E. Herold at Garrett's farm about 3 miles west of Port Royal. Booth was fatally shot during their capture by federal troops. Herold was returned to Washington, where he was executed by hanging with 3 co-conspirators on July 7, 1865.
In 1958, Richard and Mildred Loving challenged miscegenation laws in the state when they married. Although they married in Washington, DC, they returned to live in Caroline County, where they were arrested and charged under the state's anti-miscegenation statute, the Racial Integrity Act of 1924. Their case went to the Supreme Court of the United States, which in 1967 found anti-miscegenation statutes to be unconstitutional in Loving v. Virginia.
At the southern edge of the county, The Meadow, a farm originally established in 1810, became a premier facility for breeding, raising and training Thoroughbred race horses. In 1972, Riva Ridge, raised at The Meadow, won the Kentucky Derby and the Belmont Stakes, two of the three events of the Triple Crown. The following year, Secretariat, born at The Meadow, won the famous Triple Crown for the Chenery family's Meadow Stable.
In 2003, The State Fair of Virginia purchased Meadow Farm for development as a new site for the annual Virginia State Fair. Long held at locations in the capital of Richmond and Henrico County, the fair was increasingly squeezed out by expanding development around it and the growth of the event. Most recently, it was held at Strawberry Hill in central Henrico County, at the facility which became the Richmond International Raceway. Beginning in September 2009, the annual Virginia State Fair has been held at the new Meadow Event Park in Caroline County. The annual Meadow Celtic Games and Festival (formerly Richmond Celtic Games and Festival) will also be held at the new facility.
In 2009 the National Civic League presented Caroline County with one of ten annual All-America City Awards.