The county seat of Caroline County since 1803, Bowling Green is best known as the "cradle of American horse racing", the home of the second oldest Masonic Lodge, and the current location of the oldest continuously inhabited residence in Virginia.

The town of Bowling Green was earlier known as New Hope. 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. One of the first stage lines in America to maintain a regular schedule operated along this road. New Hope Tavern was built along the road in the 18th century and the area around it became known as New Hope.

The town was renamed for "The Bowling Green" which was the plantation of town founder, Major John Thomas Hoomes, who donated the land and funds for a new courthouse when the community became the county seat in 1803. The origin of the plantation's name is not definitive but may be based on the 2-acre (8,100 m²) green sward in front of the plantation house itself. The Bowling Green Estate was the site of one of the first tracks built to race horses in America. The plantation house, pre-Georgian tidewater colonial in style, was built circa 1741. A prominent colonial landmark, it is one of the oldest houses in original condition in Virginia and is listed on both the Virginia Landmarks Register and the National Register of Historic Places.

The present Caroline County Court House was built in 1835 and Bowling Green was incorporated as a town about 2 years later, in 1837. The town is best known as the "cradle of American horse racing" and as the home of the second-oldest Masonic Lodge.

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