The Religious Society of Friends of Waterford had an egalitarian view on life and believed African Americans should not be excluded from getting an education. It was because of this egalitarian view that one member, Reuben Schooley (ca. 1826-3 August 1900), agreed to sell a plot of land he owned "to the Colored people of Waterford and its vicinity." This land was purchased in 1866 with the purpose of building a school for the African Americans of Waterford and surrounding areas. Although the land was purchased in 1866, it was not until 1868 that the land was officially deeded over to a board of five trustees that had been selected by the "colored people of Waterford and its vicinity." These trustees were Jonathan Cannady (n.d.), Alfred Craven (1831-n.d.), Matthew Harvey (1824-1895), Daniel Webster Minor (ca.1836-ca.1905), and Henson Young (1843-1930).

The Second Street School was erected in 1867, two years after the end of the Civil War. The building was built by the African Americans living in and around the town of Waterford. It is likely that Quaker residents of the area helped with financial aspects of building and maintaining the school before the Freedmen's Bureau became responsible for the school. When it was built, the Second Street School was one of eight schools for African Americans located in Loudoun County and one of three schools for African Americans in the Jefferson District. In around 1870, the Second Street School became part of Jefferson District's public-school system.

The Second Street School has a few alternate names. It is referred to as the "Waterford School," the "Waterford Colored School," and "School A." The Second Street School was officially called "School A" by the Jefferson District. It was called "School A" because the African American schools in the area were given letters and the white schools were given numbers which made it easy to differentiate between them. When the school was first opened the teachers were white which was not uncommon in African American schools during the time period. In 1882 African Americans took over the teaching positions at the school. From that time on, it is presumed that only African Americans taught at the school.

Starting in 1869 the Freedmen's Bureau started requiring schools to make monthly reports. There were specific questions that were to be answered by the teachers. Some of these questions include: how many students attended the school every month, what was the average attendance of students, what area of study were the students proficient in, and what was the public opinion of the school. Class sizes at the school were large because of the lack of African American schools in the area. There was a seasonal decrease in class sizes. Male students could not attend because they needed to help with planting and harvesting crops.

The Second Street School closed its doors to students in 1957. The Waterford Foundation acquired the school in 1977 because of its historical significance to the Waterford area. In 1984 the Waterford Foundation began a living history program at the school. The program is intended for third and fourth graders to come and learn about the history of the one room school house. Waterford Foundation volunteers portray the role of a teacher at the school and recreate a school day as it would have been when the school was still open.