Oakland’s history starts on a small farm in Central Virginia when, in the middle of the 20th century, a pioneering woman opened her heart to shape new futures for students with learning disabilities.

Early Days

In 1950, after serving as an elementary school teacher, high school assistant principal, and founder of her own private school for children in grades K-2, Margaret G. Shepherd (1899-1990) started a summer camp and school for children with learning disabilities. At the time, very little was known about dyslexia and learning disabilities. However, Mrs. Shepherd was drawn to children who had difficulty reading. Students from across the south flocked to the Oakland Farm Camp and School where children used phonics and multisensory instruction to learn how to read.

The Big House on Oakland's campus.

School Founding

At the insistence of a group of parents, Mrs. Shepherd started the Oakland School in 1967 as a year-round learning disabilities program and boarding school. Mrs. Shepherd taught several students herself, specializing in helping children who, despite years of effort, had been unable to master even the bare rudiments of decoding. She excelled with these students, but her success came from more than just determining the structural analysis of words and the multisensory approach she employed; rather, she used positive reinforcement and a nurturing environment to teach students about life in general.

She believed that building students’ self-esteem was essential to their future success, along with setting high expectations and forming lasting friendships with her pupils.

Margaret Shepard, Oakland School's founder, shares The Oakland Way.

A Period of Expansion

Mrs. Shepherd’s 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.

During this time, Mrs. Shepherd continued to teach at Oakland. She was widely known as a pioneer in understanding how to teach differently wired students, authoring Phonetic and Structural Analysis: The Oakland Way in 1980.

Mrs. Shepherd remained a learner throughout her life, taking coursework at the University of Virginia and renewing her teaching certification when she was 89 years old.

In an interview just before her 90th birthday celebration, she said the following:

“I’m doing the only thing that really matters to me. Oakland, this school, these children—they’re all I really want to do. I wouldn’t have any life at all were it not for teaching.”

Modern Improvements

For the last several decades, Oakland School has continued the tradition of providing specialized instruction for out-of-the-box learners. While much more is now known about dyslexia, dysgraphia, and other learning and attention issues, Oakland continues to be a leader in successfully teaching nontraditional students using Mrs. Shepherd’s time-tested methodologies dating back 60 years in conjunction with technologies and ideas gleaned from modern research.