The year was 1959. Two friends met at the Twins restaurant in Smithfield, VA. They began to discuss the prevailing climate of education in Isle of Wight County and the need for a viable alternative to the system of the time. They wanted the best possible education for their children. For them, “best possible education” meant a strong foundation of fundamental knowledge upon which their children could build in pursuit of post-secondary education or their life’s work.

The two men, Robert L. Magette and A. Dwight Doggett, Sr., began to take their concerns to other citizens and community leaders who also felt the need for an education of the highest quality for their children. A meeting was called at the Doggett home for interested parents and, as a result of the action taken there, the Isle of Wight Educational Foundation was formed and subsequently granted a charter by the State Corporation Commission.

The management of the school was vested in a seventeen-member board of directors who were chosen because of their leadership in the various sections of the county, with each district being represented by at least one member on the board. From this board, an Executive Board was selected to facilitate the management of the school.

Until 1966, the Foundation was unable to bring its plans to fruition. In that year, the county school board decided to sell the county school located across from the Isle of Wight Courthouse. This school, once a high school and later an elementary school, was not in use as part of the county school system in 1966. The Foundation was able to purchase the five acres of land and its three buildings (a school, a gymnasium, and a teacherage) for $7,500.00 at public auction. A larger portion of land was needed in order for the school to qualify for accreditation by the state. When Mrs. Kay Porter Whitley and Mrs. Cora Taliaferro Wilson became aware of the school’s need, they donated the land adjacent to the school to the Foundation. Mrs. Whitley donated 4.1 acres which is today a part of the school’s athletic fields and Mrs. Wilson donated eight acres which is now the site of the Edward C. Jester Gymnasium and lower school playground. Mr. A. D. Doggett allowed certain land to be used by the school.

In 1966, the Board began registration for the 1967-1968 school year. Students were enrolled for grades 1 through 8. Tuition was set to be as reasonable as possible (a policy that is still pursued to this day) and bus transportation was provided. Mr. William Story, a former school superintendent, was engaged as headmaster and a staff of competent teachers was employed. All was in readiness, and Isle of Wight Academy opened its doors in September of 1967.

On Election Day 1968, a tragedy occurred. The old school, so recently purchased from the county, burned to the ground. Some of the contents of the building were saved. Sympathy for the children thus deprived of their school was felt among many citizens of the county and donations to the Foundation were numerous. In two days, the two remaining buildings had been subdivided into classrooms and the children were back in school. The Isle of Wight Ruritan Club House and the Isle of Wight Christian Church were also used to house some of the classes.

These measures, however, were only temporary. The Board of Directors with great commitment to Isle of Wight Academy decided to build anew. Three buildings were erected before September of 1969. They consisted of a lower school, an upper school and a library wing. The gymnasium, which had been subdivided for classes, reverted to its original use. The offices for the school were housed in the old teacherage. Dr. Carlysle C. Crank was headmaster during these transition years. He was followed in this office by Mr. Jack Chapman, who came to Isle of Wight from Woodberry Forest School. In 1970, Mr. William Story returned as headmaster for another year. A new building was added to house the middle school. By 1974, the student population had exceeded 500 students. A kindergarten program was begun during this time. Mr. William Hooper was headmaster during this period of rapid expansion.

The 1980’s saw a decrease in enrollment due, for the most part, to the financial crunch of the 1980’s and the rising cost of tuition. It was during this time that a pre-school and day care program was added. Mr. Don Deaton, headmaster from 1986-1990, placed much emphasis on this new program. The current headmaster, Mr. Benjamin Vaughan, reported a substantial increase in enrollment during his first year as headmaster in 1991. The 1990’s were a period of remarkable growth for Isle of Wight Academy. Enrollment nearly doubled, advanced placement and dual credit courses were offered, a new office building was built to accommodate the growing enrollment, and a comprehensive technology plan establishing two fully wired computer labs and computers in every class room was implemented.

The Academy’s athletic teams consistently won conference and state titles. Academics thrived, with students participating in state and national academic competitions, such as the Scholastic Bowl, Envirothon, and Science Bowl. A successful capital campaign, ” Building With Our Hearts and Hands,” added over 8,000 square feet of new instructional and multi-use space along with improved heating and cooling systems.

With the entire school community working together, IWA continues it charge toward progress and its future goals. Our highly successful capital campaign, “Building For The Future” focused on two major projects. In 2014, The Smithfield Foods Early Learning Center, housing preschool and kindergarten classes, opened. Also the auxiliary gym on campus was renovated and renamed the Benjamin A. Vaughan Gymnasium. Also among the completed projects and updates were a newly paved parking lot adjacent to the Jester Gym, the school-wide installation of technology such as the addition of SMART boards to every preschool-12th grade classroom as well as Chromebooks computers in all classroom grades K-12 and laptop computers and tablets in the library and available on a check out basis to individual classrooms.

The year 2017 marked a very special milestone in the school’s history-it’s 50th anniversary! At the end of the 2016-2017 session, the school faced a transition in leadership. After serving as the school’s headmaster with great integrity and dedication after twenty-seven years, Mr. Benjamin Vaughan entered a well-deserved retirement and passed over to the next headmaster, Mr. Mark Munford, a legacy of remarkable growth and service to the school

Today with over 650 students in preschool through the twelfth grade and a tradition of academic excellence in a family atmosphere, IWA is known by and continues strong as “A Family Inspiring Excellence.”