Your Impact in Action

Because of your generosity to the Annual Fund, Oakland School continues to be a place where every student thrives. Your contributions do more than support our daily operations. They actively fuel our strategic vision and create measurable progress toward our strategic goals.

Our four strategic

focus areas…

Focus Area One

Children & Curriculum

Investing directly in the classroom by expanding our Orton-Gillingham literacy programs, introducing new STEAM and executive functioning curricula, and enhancing our high school programming.

Focus Area Two

The Learning Environment

Supporting the people and infrastructure that make Oakland special by funding specialized staff professional development, accessible tuition opportunities (the Bridge Fund), and essential campus technology and grounds improvements.

Focus Area Three

Equine Program

Strengthening our unique equine programming and traditions by investing in professional training, caring for our herd, enhancing equine and executive functioning education, and expanding performance opportunities.

Focus Area Four

Our Community

Building deep, lasting connections through parent partnerships, a growing Alumni community, and strong relationships with regional and local businesses.

…and how your gifts have

made a difference so far

toward our students,

staffing, and campus.

toward our students, staffing, and campus.

Thanks to donor support, John (Math teacher) has started his specialized multisensory mathematics training program through the Atlantic Seaboard Dyslexia Education Center (ASDEC). This Orton-Gillingham-based approach will strengthen our ability to remediate dyscalculia and support students who struggle with mathematics in the same way we support students with dyslexia in reading.

Focus Area One: Children & Curriculum
One of our priorities is ensuring that every student receives evidence-based instruction designed for learners with language-based learning differences.

…and how your gifts have made a difference so far

Your support also helped us prepare our grounds—including the pool and Summerside facilities—for Oakland’s 77th Annual Summer Camp. These improvements ensure that students can enjoy a safe, engaging, and memorable summer experience while making full use of Oakland’s unique campus environment.

Focus Area Two: The Learning Environment
Investing in our campus creates safe, engaging spaces where students can learn, grow, and thrive year-round.

This spring, we built a student garden that is already producing vegetables. More than a garden, it has become a living classroom where students engage in hands-on, multisensory learning. The garden is actively incorporated into math and science instruction and provides meaningful opportunities to connect academic concepts with real-world experiences.

Focus Area One & Two: Children & Curriculum x The Learning Environment
Learning extends beyond the classroom when students have opportunities to explore, discover, and grow through hands-on experiences.

This summer, we added a Social Emotional Learning (SEL) counselor to our summer camp program. This additional support helps students build confidence, strengthen self-regulation skills, and develop healthy social connections in a safe and nurturing environment.

This summer’s SEL counselor addition confirmed our need to provide this additional level of support to our students. As such, we are hiring a full-time Social Emotional counselor as we begin the school year in the fall.