Isle of Wight Academy started in the space previously occupied by the Isle of Wight Elementary School, as a segregation academy. It was open for one year until, in the fall of 1968, a fire completely destroyed the school building, leaving only the original gymnasium. With funding from the school community, the academy was able to rebuild with four permanent classroom buildings and a new gymnasium. The academy was one of many such schools which lost tax-exempt status in the early 1970s because of racially discriminatory admissions policies. During the 1980s enrollment began to decrease. After briefly losing its tax-exempt status again in 1985 it finally regained it June 1987. In 1988, The school enrolled three African-American students out of 300, and in 1989 one. Headmaster Don Deaton told the Richmond Times-Dispatch that "We would like to have more African-American students but it's hard to attract them." The early 1990s saw a reversal of fortune for the school. Enrollment began a steady increase and more programs began to be offered to the growing student body. Enrollment now stands at approximately 650 students, the most ever enrolled at the Academy. On December 3, 2013, Smithfield Foods, a subsidiary of Shuanghui International Holdings Limited, pledged $1 million to the school for facilities and scholarships.
Mission
The philosophy is to "accept students of average or above average ability and develop them to their fullest potential by providing a quality program, which will build the student mentally, physically, and spiritually. The school emphasizes the honor, integrity, social development, and citizenship of the student."
Isle of Wight Academy has a number of extracurricular activities for the Upper and Lower School students. For the Upper School, clubs such as the Student Council Organization, Key Club, Drama Club, and Science Club have the largest degree of participation. The Upper School also has a number of academic competition teams, such as the Scholastic Bowl, Battle of the Brains, Science Bowl, Blue Crab Bowl, and Envirothon teams. The Upper School has chapters in four national honor societies, the National Honor Society, National Junior Honor Society, French National Honor Society, and Spanish National Honor Society. The Lower School has the Junior Student Cooperative Organization and the Middle School Science Club to offer academic enrichment outside of the classroom. Isle of Wight Academy offers half-credit courses in fine arts, such as Upper School Band, Chorus, and Audio Visual Technology. The Upper School participates in the Association of Virginia Academies Forensics and Fine Arts competitions, where many students place high in their respective categories.
Athletics
Isle of Wight Academy is a member of both the Virginia Colonial Conference and Metro Athletic Conference. In its history, IWA has won 70 conference season championships, 35 conference tournament championships, and 11 state championships. IWA sponsors the following varsity and junior varsity sports: football, basketball, volleyball, baseball, softball, cross country, soccer, golf, and winter and fall cheerleading. Daniel Brown attended Isle of Wight Academy, where he was a three-sport athlete. From 2005-2007, he helped Isle of Wight win three consecutive state championships. He is a tight end for the New York Jets of the National Football League.