In 1950, Margaret G. Shepherd, an experienced teacher, school assistant principal, and founder of her own private school for children in grades K–2, established the Oakland Farm Camp and School for students with reading difficulties. At a time when little was understood about dyslexia and learning differences, she recognized potential. Through phonics-based, multisensory instruction, students from across the South learned to read.

At the request of parents, Mrs. Shepherd founded Oakland School in 1967 as a year-round day and boarding school. 

In 1974, her daughter Joanne Dondero became Director, alongside her husband, Andrew Dondero, Director of Operations. Together, they expanded enrollment and strengthened campus facilities. They led Oakland until 1993.

During this time, Mrs. Shepherd continued teaching and authored Phonetic and Structural Analysis: The Oakland Way in 1980. A lifelong learner herself, she renewed her teaching certification at age 89 through the University of Virginia, proof of her enduring commitment to students.

For more than 75 years, Oakland has remained a leader in educating children with language based learning differences. While research has advanced our understanding of dyslexia, dysgraphia, and attention differences, our foundation remains rooted in Mrs. Shepherd’s time-tested methods, paired with modern research and individualized support.