The Education Foundation concept was reconstituted from a team project that had been presented in the Leadership Isle of Wight Course in 2003. Members of that team included John Graham, Dr. Michael McPherson, Judy Lemon, Bob Cole and Tom Ivy. Shortly after the completion of the team project, Dr. McPherson, superintendent of Isle of Wight County Schools, organized a meeting which included the project team members with an additional group of concerned citizens and local government leaders. As a result of that meeting, the Education Foundation for Isle of Wight County Schools was chartered in early 2004. The Foundation was established as a 501(c)(3) Virginia non-profit Corporation in 2008.

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Meeting at newly restored Boykin's Tavern, the group nominated Tom Ivy as the founding president, and named the original board of directors. Original members of the board of directors included John Graham, Bob Cole, Betty Delk, Mike McPherson, Lynn Briggs, and Kathryn Goff. Later, membership expanded with the addition of Robin Morris, Kevin Duck, Sallie Dunleavy, Steve Crawly, and Laguamna Clemons. Early projects included a sponsorship for nationally certified teachers and an early grant program for worthy class projects. Soon afterward, Martha Russ, a former educator, helped the Education Foundation to organize and hold its first charity auction in 2007. The annual Fall Gala has grown to become the premier fundraising effort for the Foundation.