Oakland School began as a one-room school built in 1900 and was called Woods School. The original school was replaced in 1920 by a two-room wooden structure located about one-half mile from the original one. The new school was named Oakland and was located on the Pipers Gap Highway, less than a quarter mile from the present brick structure.

The school population outgrew the two-room structure and from 1948 through 1953, Oakland Methodist Church housed the overflow. This overflow, the consolidation of area one-room rural schools, and the purchase of buses to transport the children to a central location, brought about the construction of Oakland Elementary School on the present site.

Oakland Elementary School, when first constructed in 1953, consisted of seven classrooms, a library with workroom, a cafeteria, and a multipurpose room with a seating capacity of 250, a principal's suite, a clinic room, and a teacher's lounge-workroom. In 1968 five additional classrooms were added to again relieve overcrowding. In addition to these facilities, there are four basement rooms which have been used as classrooms, clubrooms, and as play rooms when needed.

The school population included elementary school pupils from areas once served by Elkhorn, Farmville, Coleman, High Point, Blue Ridge, Crooked Creek, Coal Creek and the former Oakland School.

Oakland originally served children in grades one through seven. Eighth grade was taught in the school from 1956 to 1962 to relieve overcrowded conditions at Woodlawn High School. In 1969 a building program in Carroll County and reorganization of the school population into one consolidated senior high school and four intermediate schools made Oakland a school serving grades one through six. A special education class and a headstart class were added. From 1973 until 1993, the school served students in kindergarten through grade six. At the end of the 1981-82 school term, the special education program was moved to Woodlawn Intermediate School. In 1993 several Carroll County schools were closed and school boundary lines were redefined. The sixth grade at Oakland was moved to Woodlawn School and Oakland's student enrollment and staff doubled with the consolidation. An art teacher and a physical education teacher were added to the staff. With the present facilities, the school offers a comprehensive program, which provides a variety of learning experiences for all Oakland students.

A Carroll County building project was begun in the spring of 1999 and four classrooms were moved into mobile units parked in the front parking lot of the school while additions were built, and remodeling of the existing building was completed. The one-year building project extended into a second year and teachers were not moved back into the building until June of 2001. The building program remodeled the existing cafeteria and classrooms and added a new art room, computer lab, library, gym, music room/stage, office complex, clinic, 4 classrooms, and bathrooms. During this construction period of about 2 1/2 years, most teacher materials, all computers and most library books were in storage and unobtainable. The students didn't have access to the Accelerated Reading Program or computer technology, and teachers lacked their materials needed for teaching as they were allowed to keep only the minimum necessities in their rooms. Teachers were moved in and out of rooms as needed in order for the construction to take place. The staff worked in very difficult situations for 2 years with lots of moving, noise, dirt and dust, confusion, and distractions.

About the time that this building project began, the Oakland staff applied for and received a Comprehensive School Reform Grant which resulted in the implementation of a totally new math and language arts curriculum called Direct Instruction. The faculty implemented the math program the next year. This implementation and grant resulted in and involved stakeholders intensely. The school was evaluated each spring as a grant requirement with teachers, parents, and students being interviewed. Classroom teachers were observed by Appalachian Educational Laboratories, SRA consultants, other schools, and VA State Dept. of Education representative, Tony Oliviera. Due to our implementation of Direct Instruction, Oakland was nominated for the Chase School Change Award sponsored by the Fordham University, for participation in the Eighteenth Annual Excellence in Education Conference at Virginia Tech, and for a Comprehensive School Reform Demonstration Program Promising Site Award. In 2003-2004 Oakland was awarded a Reading First Grant for reading. After Christmas that year the program was implemented and Direct Instruction was no longer used.

Oakland Elementary School has been fully accredited by the Southern Association since 1972.