The northern boundary of the county borders on the Rappahannock River, notably at the historic town of Port Royal.

Developed in the colonial and antebellum years for tobacco and later mixed crops, worked by generations of enslaved African Americans, such agriculture gradually became less important.

[3] Caroline is now considered part of the Greater Richmond Region and benefited by suburban and related development.

[4] During the Colonial Period, Caroline County was the birthplace of thoroughbred horse racing in North America.

William's older brother, General George Rogers Clark, was considered a conqueror of the old Northwest Territory and a Revolutionary War hero.

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.

Just as the Civil War was concluding in April 1865, President Lincoln was assassinated in Washington, D.C., as part of a conspiracy to kill the leaders of the United States.

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.

Their case reached the Supreme Court of the United States on appeal, which in 1967 found anti-miscegenation statutes to be unconstitutional in Loving v. Virginia, based on violating due process and equal rights under the law.

At the southern edge of the county, The Meadow, a plantation originally established in 1810, became a premier facility in the 20th century for breeding, raising and training Thoroughbred racehorses.

In 1972, Riva Ridge, raised and trained at The Meadow, won the Kentucky Derby and the Belmont Stakes, two of the three events of the Triple Crown.

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.

Before development of Meadow Farm, it was held at Strawberry Hill in central Henrico County, at the facility which later 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.

[8] In 2009 the National Civic League presented Caroline County with one of ten annual All-America City Awards.

The county is home to a quarry that has proved a rich source of pre-historic whale and shark skeletons.

New businesses and developments include Remuda Programs for Eating Disorders, The Virginia Sports Complex, the multi-national electrical contracting firm, M.C.

Caroline County is represented by Republican Ryan T. McDougle in the Virginia Senate, Republicans Robert D. "Bobby" Orrock, Hyland F. "Buddy" Fowler, and Margaret Bevans Ransone in the Virginia House of Delegates and Democrat Abigail Spanberger in the U.S. House of Representatives.

One of the earliest stage roads in the colony ran through the area from Richmond to the Potomac River, where a ferry crossing was operated to Charles County, Maryland.

[21] The present Caroline County Court House was built in 1835, and Bowling Green was incorporated as a town in 1837.

Bowling Green is located along Virginia State Route 2, one of the two earlier highways between Richmond and Fredericksburg.

In 1941, the United States government acquired 77,000 acres (310 km2) of Caroline County to the north and east of Bowling Green.

It was first established in 1652 as a port on a navigable portion of the Rappahannock River during an era when waterways were the major method of transportation of people and property in the British Colony of Virginia.

Dorothy Roy and her husband John owned a warehouse chartered by the crown, a ferry service across the Rappahannock River to King George County and a tavern.