By the end of the 1960s, Caswell County's public schools were beginning to fully integrate. A decade and a half earlier in 1954, the U.S. Supreme Court ruled in Brown v. Board of Education that racial segregation in public schools was unconstitutional. In a later decision by the Court in May 1955 known as Brown II, school districts were given the ambiguous order to desegregate "with all deliberate speed."^[8] Like many school boards in the South at the time, the Caswell County Board of Education interpreted the Court's ambiguity in a manner that served to delay, obstruct, and slow the process of racially integrating its schools.^[9][10]

The Board of Education's resistance to integration had already been emboldened by North Carolina's passage of the Pupil Assignment Act in April 1955. The legislation gave county school boards full school placement authority.^[10] Driven by the act's power, the Pearshall Plan's passage, and the prevailing anti-integration sentiment of the white community, the school district kept assigning children to schools in a segregated manner.^[11]

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. Undeterred, the parents organized protests that included the NAACP. A federal lawsuit was subsequently filed in December 1956 asking for the immediate desegregation of Caswell County and North Carolina schools.^[12]

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.^[13] The school board denied their applications and continued to reject them through 1962.^[11] Nevertheless, the federal lawsuit kept moving forward.^[14]

In December 1961, U.S. District Court Judge Edwin M. Stanley ruled that two brothers, Charlie and Fred Saunders, could promptly attend Archibald Murphey Elementary School, a now-closed formerly all-white school near Milton. When the new semester began in January, however, they did not present themselves for enrollment. The Ku Klux Klan had sent a threatening letter to the Saunders family previously.^[15] According to an affidavit submitted by the children's father C.H. 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. Saunders also conveyed that he would be agreeable to transferring schools if his children's protection at Murphey Elementary could be assured.^[15]

A year after the Saunders decision, Stanley ruled that the school district had been improperly administering the Pupil Assignment Act. In December 1962, he told the school boards of Caswell County and the city of Durham to allow every schoolchild complete freedom of choice regarding school placement.^[16] On January 22, 1963, sixteen African American schoolchildren enrolled in four of the county's previously all-white schools.^[11]

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. He was pursued and menaced by the men as he drove home. After a rear-end collision, the other vehicle's driver emerged with a firearm. Fearing for his life, Brown shot and wounded two of the men in an exchange of fire before turning himself in to police.^[17][11] Due to the circumstances, Attorney General Robert F. Kennedy was soon informed of the incident.^[18]

Several months later, Brown was convicted of assault with a deadly weapon and served 90 days in jail. While awaiting trial, white men bombed his yard.^[19] His four children and the 12 others who integrated the county's schools were physically threatened and emotionally abused throughout the semester. Despite requests from the NAACP and concerned families, no police protection was provided. Furthermore, the Board of Education refused to arrange school bus transportation.^[20][11]

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.^[21][11] While there had been some faculty integration, the less than two percent enrollment rate in essence preserved segregation. The school district's integration plan had not fostered sufficient desegregation.^[22] 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.^[22] If they did so, they faced social stigma, severe discrimination, and other hardships. Consequently, many families, though supportive of integration efforts, chose to keep their children safe in valued Black schools such as Caswell County High School.^[23][11]

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. The bureau began taking steps to cut off federal funding.^[24] The school district was not in full compliance with federal integration standards until 1969.^[25] In that year, the Caswell County Board of Education implemented a plan for complete desegregation after Judge Stanley ordered the school district in August 1968 to integrate starting in the 1969–1970 school year.^[26][27][11]

When school integration and consolidation subsequently occurred, Bartlett Yancey High School in Yanceyville became the only public high school in the county after Caswell County High School's closure in 1969.^[28] The closed high school building's educational use was promptly reconfigured. The new integrated school was named N.L. Dillard Junior High School in honor of the former high school's principal. Integrated elementary schools were established based on zoning.^[25]