Oakland History

A Pioneering Spirit

Margaret Shepherd
Margaret Shepherd

Margaret Shepherd Oakland’s founder, Margaret G. Shepherd, was a teacher for more than 60 years. After serving as an elementary school teacher, high school assistant principal and operating her own private school for children in grades K-2, Mrs. Shepherd started a summer camp and remedial school for children with learning disabilities on her family farm in Central Virginia in 1950. Students from across the south flocked to the Oakland Farm Camp & School where children learned how to read. She later added a year-round learning disabilities boarding school program as well as a day school program. Mrs. Shepherd was a pioneer in many ways. She was drawn to children who were experiencing trouble reading. In those days, very little was known about dyslexia and learning disabilities. She created a program that used phonics to teach reading and positive reinforcement to create a nurturing environment that enabled personal growth and development. For her, building self-esteem in students was the very foundation of successful education, as was forming true and lasting friendships with her students and setting high expectations.

Many of the methods used to teach the very first Oakland students are still in practice today and regularly are enhanced. Up until the end of her life, Mrs. Shepherd continued to teach. At age 91, she was the main teacher for a handful of students who presented the greatest challenge. Where other schools, including other learning disabilities schools, had failed with certain children, she was extremely successful.

In 1967, at the insistence of a group of parents, Mrs. Shepherd began a year-round program including a learning disabilities boarding school. Her daughter, Joanne Dondero, became the school’s director in 1974. Mrs. Dondero, along with her husband, Andrew Dondero, who served as director of operations, ran Oakland until 1993. Their tenure was marked by an expansion of school enrollment to the current capacity as well as construction of a variety of new facilities.