The Hillsboro community has offered educational opportunities to the youth of Hillsboro since the 1840s. By 1846, John Jonas Potts had established a day and boarding school and in 1858 John Josiah White opened a school in the basement of the new Methodist Church. Both schools had to close during the Civil War. In 1867, the first public school in the community opened in a small stone building built on property donated by Michael Arnold. In 1830, Dr. J. E. Copeland first taught five month sessions in this school.
Mrs. J. B. White was the first principal in the Locust Grove Academy, Hillsboro's old stone school built in 1874, which still stands on the grounds of the current school. In 1917, the Locust Grove Academy was enlarged. In 1918 a Junior High School was established at this location and remained in operation until 1935. A second addition, a brick auditorium, was added in 1929.
In 1911, Hillsboro became the first community to consolidate students from several smaller schools in the area and begin a school bus (horse drawn) service to Locust Grove Academy.
Built on a lot next to the Academy, the current school building, unique in its circular design, opened to students in 1966. The historic stone and brick "Locust Grove Academy" became known as the 'Old School" and was used as a community center. There was a teacher for each grade and Mr. Ralph Kilmer was the part time principal. Mr. Benton Wicks was named full time principal in I971 when Loudoun County adopted the middle school concept and Hillsboro became an "elementary" school.
The principals of Hillsboro Elementary School who followed Mr. Benton Wicks weere: Mr. J. D. Hart (1973-1983), Mrs. Evelyn Collier (1983-1985), Mr. Kenny Vance (1985-January 1990), Mr. Jerry Hill (January 1990 - January 1995), Mr. Lou Tiano (January 1995-1997), V. Joyce Smith (1997- 2002), Julie McKay (2002-2004), and Dave Michener (2004 - 2016).
The Hillsboro Elementary School was closed by Loudoun County Public Schools after the 2015-2016 school year.
The Round school is now occupied by the Hillsboro Charter Academy, and started with Trisha Ybarra-Peters as the principal in the fall of 2016. Mark Wertheimer, the current principal, came on July of 2017.
Today, Hillsboro is faced with new technology and a rapidly growing school system in Loudoun County. The community has a long history of support for education, beginning before the Commonwealth of Virginia recognized the need for and provided a law to establish free public education in the commonwealth. Hillsboro School will continue to seek community support as we face these new challenges.
Hillsboro is one of the loveliest and most historic spots in Loudoun County. There are many stone houses in Hillsboro that date back to the 18th century. You will find picturesque settings, steep mountain slopes that rise on both sides of the road, Catoctin Creek along the southern border and many other physical features that have helped Hillsboro age more gracefully than any other small town in Loudoun. The most outstanding sight is the magnificent backdrop of the Blue Ridge Mountains.
Hillsboro is unique in the county for the large number of families who have remained in the area, often on the original land grants, since the 18th century.