We believe in Oakland’s value as a transitional school, a concept that begins the moment your child is accepted to our time-tested program.

First, we ready our students for what comes next by crafting individualized learning plans designed to challenge children in their areas of strength and build both confidence and skills in areas where they may not be as strong. Frequent check-ins help monitor each child’s academic, social, and emotional growth, and positive reinforcement encourages a love of learning beyond Oakland. Along the way, we continuously set new academic goals for each child.

This instills a sense of achievement that prepares students for transition to a more traditional classroom environment.

At Oakland, students learn to truly understand and articulate their own identity, empowering them to step confidently into new school settings and social situations. Whether in eighth grade, or when the student demonstrates readiness for the next step in their academic journey, an Oakland graduate exhibits the following:

  • Responsibility

  • Work Ethic

  • Flexibility

  • Critical Thinking

  • Initiative

  • Perseverance

  • Teamwork

  • Respect

  • Humility

Two Oakland students focus on a game of Jenga.

After Oakland

From nearby Charlottesville and Albemarle Country to as far away as Alaska, our graduates have gone on to attend public schools, boarding schools, and independent day schools around the country.


Boarding Schools

  • Admiral Farragut Academy · St. Petersburg, FL

  • Arthur Morgan · Burnsville, NC

  • Blue Ridge School · Dyke, VA

  • Chapel Hill-Chauncy Hall School · Waltham, MA

  • Christchurch School · Christchurch, VA

  • Eagle Hill School · Hardwick, MA

  • Fishburne Military School · Waynesboro, VA

  • Foreman · Litchfield, CT

  • Foxcroft School · Middleburg, VA

  • Greenwood · Putney, VT

  • Grier School · Tyrone, PA

  • Maplebrook School · Amenia, NY

  • Massanutten Military Academy · Woodstock,VA

  • Middlebridge School · Narragansett, RI

  • Miller School of Albemarle · Albemarle, VA

  • Oak Creek Ranch School · West Sedona, AZ

  • Oak Hill Academy · Mouth of Wilson, VA

  • Oldfields School · Glencoe, MD

  • Purnell School · Pottersville, NJ

  • Riverview · East Sandwich, MA

  • Virginia Episcopal · Lynchburg, VA

  • Woodhall School · Bethlehem, CT

Independent Day Schools

  • Afton Christian School · Afton, VA

  • Charlottesville Catholic School · Charlottesville, VA

  • Chesapeake Academy · Irvington, VA

  • Commonwealth Academy · Alexandria, VA

  • Covenant School · Charlottesville, VA

  • Denver Academy · Denver, CO

  • Field School · Crozet, VA

  • Gaston Day School · Gastonia, NC

  • McLean School · Potomac, MD

  • New Community School · Richmond, VA

  • New School of Northern Virginia · Fairfax, VA

  • Oakwood School · Annandale, VA

  • Parkmont School · Washington, DC

  • Renaissance · Charlottesville, VA

  • St. Anne's Belfield · Charlottesville, VA

  • St. Edward's School · Vero Beach, FL

  • Steward School · Richmond, VA

  • Tandem Friends School · Charlottesville, VA

  • United Christian Academy · Stanardsville, VA

  • University Lake School · Hartland, WI

Here’s what Oakland alumni have to say.

"To me, Oakland is much more than a school, it’s an institution that molds entire futures. Coming into Oakland with a plethora of learning differences, Oakland has not only helped me academically but truly helped me better understand myself and my capabilities. From the start, each student is informed that 'can't' isn't an excuse and that greatness is in everyone’s future. At Oakland, teachers believed in me, allowing me to believe in myself."

Max S., Oakland Alumnus

"This place is great, made friendships that I have kept to this day, don't know where I would be without Oakland school. The staff is companionate and the teachers want to see you succeed. Overall, this place is the best."

Ezra K., Oakland Alumnus

"Graduated in the summer of 1989 after two full years there that changed my life for the better. Couldn't have made it without the great people of Oakland School. Loved my time there. Made me the man I am today."

Andrew S., Oakland Alumnus

"At Oakland, I transformed from a little, shy girl who got bullied because I could not read like the other kids to feeling safe and happy at a place where everyone was treated the same. The first day I toured Oakland, I felt at home and for once could just be me. The feeling that Oakland is home still has not changed even years since graduating. Oakland gave that shy little girl confidence, friends that understood, and the tools to learn."

Emma B., Oakland Alumna