[12] Middle-class families accounted for less than a fifth of the settler population and were chiefly involved in business entrepreneurship, craftsmanship, small-scale commercial farming, export, and trade.

[13][10] They actively promoted business and settlement in and around towns such as Leasburg, Milton, and numerous villages to further local economic development and their own upward social mobility.

[21] Until the early 1800s, tobacco was harvested mainly as a secondary crop by the settlers depending on changing market demand, pricing, soil exhaustion, and other variables.

[23] Their merchants offered good tobacco prices initially but eventually reduced them greatly, causing many planters to fall into substantial debt, which could not be repaid without selling land or enslaved people.

[30] The county was named for Richard Caswell who was the first governor of North Carolina after the Declaration of Independence in 1776, a delegate at the First and Second Continental Congresses, and a senior officer of militia in the Southern theater of the Revolutionary War.

[31] The legislative act creating Caswell ordered its first court to be held at the homestead of Thomas Douglas and appointed commissioners to find a permanent location to build a county courthouse and prison.

County residents renowned for their Revolutionary War service include Lieutenant Colonel Henry "Hal" Dixon, John Herndon Graves, Dr. Lancelot Johnston, and Starling Gunn.

During this period, the county saw the creation of new flour and lumber mills and experienced the furniture output of Thomas Day, a free Black businessman in Milton.

[36] In 1839, on Abisha Slade's farm in Purley, an enslaved man named Stephen discovered the bright leaf tobacco flue-curing process.

The following year his farm harvested 20,000 pounds (9,100 kg) of bright leaf tobacco on 100 acres of land and the crop was sold in Lynchburg, Virginia, at an exorbitant price.

[17] Roosevelt's New Deal programs during the Depression years, improved farming techniques starting in the 1940s, and the economic impact of World War II also contributed significantly to revitalizing the area.

[36][30] After World War II, as Caswell County and the broader United States returned to civilian life, it became evident that new efforts were needed to overcome old economic barriers.

What is more, the heritage of the county's earlier Boom Era of bright leaf tobacco and Greek Revival architecture represented both an opportunity and a hindrance.

[54] Due to the Emancipation Proclamation in January 1863, enslaved African Americans in Confederate territory were recognized as free individuals by the executive branch of the U.S. federal government.

However, in 1866 restrictive state laws called "Black Codes" were passed in North Carolina by former Confederate legislators who had returned to power as Conservatives.

[64] The 1868 constitutional convention passed resolutions that included the abolition of slavery, the adoption of universal male suffrage, the removal of property and religious qualifications for voting and office holding, and the establishment of a uniform public school system.

Because the convention gave North Carolina a new constitution in 1868 that protected the rights of African Americans, the state was readmitted to the Union that same year on July 4 upon ratification of the Fourteenth Amendment.

[57] As Klan violence in Caswell County escalated in 1870, the Republican state senator of the area, John W. Stephens, became increasingly fearful of attack.

[67] Wiley had secretly agreed to work with the Klan and lured Stephens into a trap, whereby he was choked with a rope and stabbed to death by Klansmen in a vacant courthouse room.

[81] In response to these developments, fifteen local African American parents presented a petition to the school district in August 1956 calling for the abolition of segregation, which the board refused to consider.

[82] In August 1957, 43 local students, many of whom were plaintiffs via their parents in the federal court case, applied for admission to public schools that were closer to their homes than the segregated ones they had been assigned.

Saunders Sr., the KKK's threats caused him to miss a school board reassignment hearing ordered by the judge in August 1961 prior to his final judgment.

[81] On their first day of school, a group of white men harassed and threatened one of the parents, Jasper Brown, who was a local civil rights leader and farmer.

[90][81] By late 1967, only 57 African American children out of a Black student population of approximately 3,000 were attending integrated public schools in Caswell County.

[92] Its "freedom of choice" plan put the onus of integration on individual African American students and parents, who had to opt to cross the color line themselves.

[77][81] The school district's low integration rate resulted in the U.S. Office of Education citing the county in 1966 as one of seven in the state that were not in compliance with its civil rights Title IV guidelines.

Such politicians include Donna Edwards, Archibald Debow Murphey, Romulus Mitchell Saunders, and Bartlett Yancey, Jr.[98][99][100][101] Legislators from the county had considerable influence on state politics during the first half of the 19th century.

Before entering Congress, she was the executive director of the National Network to End Domestic Violence, which provides advocacy and legal support to battered women.

[133][50] Caswell County's agricultural sector produces hemp, tobacco, soybeans, corn, wheat, oats, barley, hay, alfalfa, beef cattle, sheep, swine, and poultry.

[159][160] The Spring Fling is a two-day event and is held on a weekend in late April or early May on the grounds of the Providence Volunteer Fire Department.